Sweet Retreat

Sweet Retreat: Walk to Ocean, Town, & Eateries - Parking, Smart TV, Fast WiFi

2 BR
1 Bath
Sleeps 6

Renovated and newly furnished condo in the heart of downtown Marblehead. From your front door, you are next to a restaurant, steps to a movie theater, and in the middle of all that Marblehead has to offer. Great food, great shopping, amazing history, art, and culture. Marblehead is famous for amazing boating, antiquing, art and history. All this, and a quick bus, uber or car ride to downtown Salem.

Guests staying at Sweet Retreat enjoy the perfect balance between modern amenities in an historic building; between vibrant downtown location with quick access to the sea and golf. As the birthplace of the US Navy, it's no wonder that Marblehead hosts internationally acclaimed sailing races. For history and antique buffs, you'll find Marblehead to be quite the delight. Enjoy an amazing array of distinct boutiques, art galleries, and antique shops.

Sweet Retreat has just completed a full renovation converting this antique colonial (circa 1759) into a contemporary living space. Guests staying at Sweet Retreat enjoy open concept living with a full sized dining area and fully-applianced kitchen, full sized laundry, and living room with big screen smart TV.

For sleeping accommodations, there are 2 bedrooms, each with a king size bed. One couch opens into a queen size sleeper.

Come enjoy Marblehead - one of Boston's North Shore precious gems!

Special Note about Parking:

There are 2 off-street parking spaces for Sweet Retreat behind the building. Please be aware that the driveway is very narrow. At its narrowest point, it is only 7-feet 10-inches wide. We recommend that you use this parking only if you have medium-sized or smaller vehicle. Most vehicles will need to retract mirrors to fit through the narrowest point.

Special Note about accommodations: living space is on the second floor. Bedrooms and bathroom are on the 3rd floor.


SLEEPING ARRANGEMENTS (maximum occupancy of 6):

Sweet Retreat has 2 bedrooms.

Front Bedroom - sleeps 2

- King size bed with 2 bedside tables and 2 lamps.

- Large Walk In Closet

Back bedroom - sleeps 2

- King size bed nestled between 2 bedside tables, both with a lamp.

- 1 Large Closet

- Luggage rack

Living Room - sleeps up to 2 in a queen sleep sofa. The sofa can be opened into a queen bed.

Please notify us if you want the extra linens for the sleep sofas & guests (a small fee applies)

Main Shared Bathroom

- Tiled walk-in shower with mounted handheld showerhead


Sweet Retreat Accommodation Highlights:

- Fully-equipped granite kitchen with full size appliances, Keurig coffee maker, blender, washer/dryer, & more!

- Filtered water - bring your favorite water container. The whole accommodation provides filtered water from all faucets. No need to buy water here!

- Living room with Big Screen Smart 50" TV, comfy seating

- Ultra Quiet washer & dryer located on main floor

- High Speed WiFi

-Smart TV for easy access to your personal streaming services

- Off-street parking for 2 cars (note comments about narrow driveway)

Special Note: For your safety, Exterior Security Cameras are present at this accommodation.


About Marblehead

Founded in 1629, Marblehead was a crucial fishing port during the American Revolution; much of its history can be discovered by navigating through the colorful, narrow streets of Old Town. Like an open-air museum, Marblehead flaunts its history not only in its well-preserved 18th-century houses and architecture, national historic landmarks and local shops are sprinkled throughout the town.

After meandering amongst the quaint Colonial houses, take a tour through Marblehead Neck, which leads to the lighthouse. Marvel at the breathtaking views of Marblehead Harbor, birthplace of the US Navy, & a major sailing capital.

Marblehead’s most popular beach, Devereux, has plenty of picnic tables, playgrounds, and on-site restrooms. Gas House Beach is on Little Harbor. With a rocky shore and small boats anchored in tranquil, shallow water, the scene at Gas House is perfectly New England. Active visitors can enjoy a paddle at King’s Beach with views of Boston.


About iTrip North Shore Properties

- Smoking is strictly prohibited. Guests will be fined and immediately evicted for smoking or vaping in the home or on the property.


These are cause for eviction with no refund. If any damage impacts our ability to offer the home for future guests, you will be held liable.



- Each of property features a starter set of supplies for guests which includes toilet paper, paper towels, dish detergent, & hand soap.

- The beds are fully made & ready for your arrival with freshly laundered linens. A set of towels for each registered guest are included in the rental rate.

- For family friendly homes, a luxury Pack-n-Play or other children's furnishings are available for an additional charge (as availability permits).


Visiting like a local means being neighborly. Please be respectful of the owner's home and considerate of the neighbors.

139 Pleasant Street, Unit 2 Marblehead, MA 01945
Registration Number: C0038271680

Sleeping Arrangements

Front Bedroom King
Rear Bedroom King
Living Room Sofa Queen

Bathroom Configuration

Main Bath: Shower, Toilet

Property Rules

Check In: After 4pm
Check Out: Before 10am
Smoking: Not Allowed


Air Conditioning
Bathroom Step Free Access
Bed Linens
Big Screen TV
Carbon Monoxide Detector
Central Air Conditioning
Central Heat
Children Welcome
Cleaning Disinfection
Clothes Dryer
Coffee Maker
Cooking Basics
Deadbolt Lock
Dining Table
Dishes And Utensils
Dishes and Silverware
Emergency Exit Route
Ethernet Connection
Extra Pillows And Blankets
Family Friendly
Fire Extinguisher
First Aid Kit
Free Full Kitchen
Hair Dryer
Internet Access
Iron Board
Keyless Entry
Kid Friendly
Living Room
Long Term Stays Allowed
Outdoor Lighting
Patio or Balcony
Pets Not Allowed
Private Entrance
Private Living Room
Requires Stairs
Satellite or Cable
Self Check-In Checkout
Smart TV
Smoke Detector
Smoking Not Allowed



Frequently Asked Questions

For your security, Sweet Retreat has exterior cameras recording video.
  • A walk or bike ride along the Marblehead Rail Trail, a 4-mile long pathway that meanders through wooded areas and continues on into the neighboring towns of Swampscott and Salem.
  • A walk through the Marblehead Neck Wildlife Sanctuary, located just 1/4 mile from Sweet Retreat, offering a one mile trail through 20 wooded acres, with the opportunity for bird and animal sightings.
  • A visit to Devereux Beach, Marblehead’s largest beach, which offers a playground, restaurant, picnic tables, and parking. Lifeguards on duty during specified hours. 
  • Renting stand-up paddle boards at Riverhead Beach and exploring the boats and sites in Marblehead Harbor.
  • Eating in Marblehead’s many restaurants, from waterfront dining at the Landing to seafood at the Barnacle or sandwiches and pizza at Cafe Vesuvius.
  • A visit to one of Marblehead’s many beautiful oceanfront parks, including Chandler Hovey park (featuring the Marblehead Lighthouse), Castle Rock (for the climb and the views), and Fort Sewall (for the scenery and the history).
  • A visit to one of Marblehead’s many historical sites, including the Jeremiah Lee Mansion, the King Hooper Mansion, Old Burial Hill, the Old Townhouse, and Abbot Hall (home of the painting the Spirit of ’76). 
  • Wandering through Marblehead’s two quaint shopping districts, one newer and one dating from the 1600s, with both offering a variety of dining and shopping options.
  • Exploring the older part of Marblehead at the far end of the peninsula, with many houses bearing plaques dating from the 1600s and providing information about the original owner’s name and occupation.
  • A visit to one of Marblehead’s many playgrounds, including Gatchell’s, Hobbs, and Gerry, with climbing structures and slides as well as open fields for children and adults to enjoy. 
  • A movie right in the heart of Marblehead at the Warwick Theater.
  • The Salem Witch Museum, Witch House, and Witch Dungeon offer educational insights into the witch trials that took place in Salem in the 1600s.
  • The world class Peabody Essex Museum with a variety of unique exhibitions from around the world.
  • The House of the Seven Gables,  well known as the setting of Nathaniel Hawthorne’s novel of the same name.
  • Pickering Wharf, a harbourfront shopping and dining district offering views of beautiful boats and the opportunity to stroll to the end of the nearby pier, ideally after first stopping by Captain Dusty’s for some homemade ice cream.
  • Salem Willows, which offers ocean front parks, beaches, and walking paths as well as an old fashioned arcade, including a carousel and miniature golf course. 
  • A variety of specialty walking tours are available, many focusing on the Salem Witch Trials.
  • Boat and trolley tours also offer the opportunity to explore Salem by land or water and learn about the town’s history.
Sweet Retreat provides high-speed internet services.  Internet services have been shown to meet the needs of guests traveling for both work and pleasure.  
Regrettably, Sweet Retreat does not host furry family members.  That is, Sweet Retreat is strictly no pets.
As a token of our appreciation, a Welcome Pack awaits you in the fridge.  

Beds are made with freshly laundered linens. Clean towels for each registered guest are placed on the beds. Please bring your own beach towels. Each accommodation comes with  starter pack of 1 roll of paper towels, each bathroom will have at least 1 spare roll of toilet paper.  A starter pack of coffee, cleaning supplies, and hand soap is also provided.

Items you should bring with you: Extra paper products, beach towels, beach chairs, sunscreen, toiletries, food, beverages, and any other essentials and assundries to make your vacation enjoyable.
The City of Marblehead offers paid parking lots.  You can download the Passport Parking app and have the ability to pay for parking without leaving the comforts of Sweet Retreat.  Below please find some useful information on the pay by plate kiosks, times of operations, locations, and more.
There are one or more kiosks in each parking lot. There is an easily identifiable sign “Pay Here” above each kiosk. 
  • Pay at the kiosk, with cash or credit card 
  • Pay by phone, through the Passport Parking App, available on these Play Store and Apple App Store.
Kiosks operate 24 hours/day

Free parking lots are at the Train Station and 2 Blue Lane Road on Rt 127.  
During the winter, meters and kiosk parking is free.  All seasons, on-street parking outside of the meter and kiosk areas are free.
Welcome!  We hope you will stay with iTrip North Shore.  We would be delighted to be host your visit! iTrip North Shore strives to provide excellent service and assistance. 

Guests are expected to honor our House Rules to be Good Neighbors and Respectful Visitors.  
Good Neighbors honor the right of Sweet Retreat’s neighbors to peacefully enjoy their homes. iTrip North Shore's guests will:
  1. Respect Quiet Hours: Quiet Hours are dictated by local rules and ordinances.  Unless specified otherwise, quiet hours are between 10PM and 8AM. 
  2. Not Host Events or Parties: without express written approval from iTrip North Shore, do not host any parties or events. 
  3. Follow the Law: do not do anything illegal.
  4. Respect Boundaries: Do not encroach into the neighbors’ space, including but not limited to yards, gardens, decks, patios, and parking spaces.  Do not use neighbors’ amenities or take neighbor’s property, such as: furniture, grills, pools, spas, etc.
  5. Follow Parking Instructions: Please follow all parking instructions and only use those spaces allotted to Sweet Retreat.
Respectful Visitors: remember you are renting a private home; iTrip North Shore guests will treat Sweet Retreat with the same or more respect that they would like shown to their belongings:
  1. Prudent Use: instructions on how to use appliances and amenities are provided.  Please use all items for their intended purpose and per instructions.  Please contact iTrip Vacations North Shore Massachusetts if you have any questions.
  2. Be Neat and Caring: please do pick up after yourselves; put trash and recycling in proper bins, do the dishes, use coasters, and leave the furniture where it belongs. 
  3. Park in Designated Areas: Please do park in driveways, parking pads and garages.  Please do not park on lawns or in gardens.
  4. Do Not Smoke or Vape: smoking or vaping of anything: cigarettes, pipes, cigars, or marijuana, requires special remediation to remove the aroma.
  5. Do Not Tamper with Safety Sensors: iTrip North Shore homes come equipped with a variety of safety sensors, such as: exterior cameras, noise monitoring, smoke detectors, carbon monoxide detectors, and more.  Respectful guests do not tamper with the owner's safety sensors.
  6. Be Careful: where there are wet area amenities such as waterfronts, docks, pools, or hot tubs, please take care to secure the areas and take appropriate precautions.
  7. Return Keys/Passes/Remotes: please return items as described in Check-out instructions.   
Please know that violating House Rules is grounds for terminating our agreement.
Please enjoy this lovely home with respect for the home and the neighborhood.
Enjoy your stay!
Minimum age for guests booking our properties is 25.


Wonderful Time!
4/5 stars
We truly enjoyed our stay at Sweet Retreat! Had we known just how much we were going to enjoy our stay, we would’ve booked longer. Comfy beds, shower is great and the area is amazing. It is on a very, busy street so the back bedroom is much quieter! Believe it when you read that it is a tight squeeze to get to the parking spot! We drove a CRV and it was tight. Anything wider won’t fit!
- Charlene

Hi Charlene, Sweet Retreat is perfect when you want to explore the historic district of Marblehead or even to be close by to Salem as well. Didn’t you love the central air conditioning that the property offered during those warmer days? We are so glad to hear you enjoyed your time with us and would love to have you back soon!

- Manager Response
5/5 stars
Lovely place to stay right next to the available night life. Convenient to walk to stores and shops.
- Brody

Hi Brody, Sweet Retreat is a gorgeous home so close to the historic district of Marblehead. There is so much to see while staying there, and with only about a 15 minute drive to Salem, it’s perfect for plenty of adventures. Didn’t you love the spacious living room and home away from home feeling? We hope to see you again soon!

- Manager Response
Wonderful stay
5/5 stars
We loved our stay at Sweet Retreat. The location is perfect to visit Marblehead. The retreat has all the amenities , charm and lovely decor . We met the owners who were helpful with parking and a warm welcome .
- Michael

Hi Michael, Sweet Retreat is truly a cute little home, a perfect place to stay when you want to go out exploring nearby. We are so happy to know that you enjoyed your stay and that the owners were there to be helpful and welcome you wholeheartedly. We would love to host your stay again soon!

- Manager Response
Wonderful condo!
5/5 stars
Got this condo for my parents! Very nice and clean - great location and just a block away from everything you need! You can walk to the beach as well! The host was very accommodating and we overall had a great experience! Will def rent this again!
- Cynthia

Hi Cynthia, It's great to hear how much you enjoyed Sweet Retreat, it is truly a cute home to enjoy when you want to be in the historic Marblehead and close by to Salem. We just love how comfortable the home is with plenty of space to enjoy. We truly hope to host your stay again soon in the future.

- Manager Response
Perfect spot for a girls trip!
5/5 stars
This place was PERFECT! We had 7 girls in our group with the main plan to tour around Salem. It was a short drive/uber in to town. Marblehead itself was also a gorgeous spot, the neighborhood is clean and nice. As for the house, it was very clean and well decorated. We brought our own air mattresses as per the other reviews. Had no issues with anything! We really had such a lovely time here, I would definitely recommend this place :)
- Kris

Hi Kris, We are so elated to hear that you enjoyed your stay with us at Sweet Retreat, it is certainly a wonderful space to stay at when you want to do some exploring close by to Salem. Didn't you love being just a short walk to the ocean? We truly hope to see you again soon!

- Manager Response
5/5 stars
Absolutely perfect! We wish we could've stayed longer. Hopefully we can go back to the Sweet Retreat again no matter the season 😊
- Lisa

Hi Lisa, We are so thrilled to hear that you enjoyed your stay with us at Sweet Retreat. We love how open and beautiful the home is, a truly welcoming place to be any time of the year. Didn't you love being able to take a a short walk to the beach and enjoy the sand between your toes and the relaxing smell of sea salt? We truly hope to see you again soon!

- Manager Response
A wonderful stay!
5/5 stars
We had such a wonderful stay! There’s so much to do and see. We loved the house it was perfect. Our daughters really enjoyed it as well 17 and 7. There’s a nice restaurant right outside the door and a very cool crystal shop below you! Lots of stuff in walking distance! I would rate 10 stars if I could!
- Heather

Hi Heather, We are so happy to hear how much you and your family enjoyed their time at Sweet Retreat. We truly appreciate your feedback as we strive to ensure each and every one of our guests are thoroughly enjoying their time at our properties. Didn't you love how cozy and homey the property felt while staying there? We truly hope we get to see you again soon!

- Manager Response
Great location, even better host!
5/5 stars
This location was right in the heart of Marblehead, with plenty of bars, restaurants, coffee spots, and shops. This beautiful, safe, and quiet town was the perfect spot for our vacation. The host was on top of everything we needed, and the place was incredibly clean. Easy instructions on check out, and all around great stay! Would definitely recommend, and would stay here again!
- Zak
Great Extended Stay
5/5 stars
We stayed for 2 weeks while exploring the North Shore. Very comfortable beds, adequately furnished including the kitchen. We had no issues at all but a couple of things to be aware of, The driveway was as advertised and very tight, caused some issues when we had guests (and inexperienced drivers), but there is some free street parking a block or so away; A flight of stairs to get in, living room gets a bit tight with 6 people. That being said we had a great stay, walkable to restaurants and all the necessities and the waterfront (about a 15 minute walk) and a bus stop right outside. Everything was in working order and the beds were exceptional.
- Dan
Excellent condo
4/5 stars
Very clean, well supplied. Nice layout. Didn't use television, nor appliances. Beds super comfortable. Provided a fan I requested, needed white noise. Only draw back, it was between 2 bars, and seem it was May 4th, there was a lot of partying. Very loud night. We didn't stay both nights.
- Patricia

Sweet Retreat is an amazing little spot and I wholeheartedly agree about the beds being comfy! With your stay falling over Cinco de Mayo, I get that it was a little louder than usual (it was also one of the warmer times we have had so far this year!). So glad that we were able to provide a voucher towards a future stay to welcome you back again and help make up for you having to leave early! - Eli / iTrip North Shore

- Manager Response
5/5 stars
We love it here!!
- Carol
Everything was great!
5/5 stars
We absolutely loved staying here. The house was well equipped for us and our toddler and was cozy yet spacious enough for him to run around and play. We loved the proximity to Salem and when we come back we will definitely try to stay here again!
- Summer
Perfect get away
5/5 stars
The condo was perfect. Close to shops and bars. Easy to get into salem from here. We ubered into Salem several times and it was an easy 15 min commute. The added touches of coffee k cups and bottled water in the refrigerator was much appreciated. Thank you so much for letting us stay in your beautiful place.
- Jeanna
Home sweet home
5/5 stars
Perfect spot for a weekend in salem. Cute little crystal shop right below. House was clean and decorated nice. Owner was super friendly. Overall eat place to stay.
- Kerri
4/5 stars
Our family stayed here for 5 nights. We enjoyed the location and even though the apartment is on a busier street, the stay was quiet. The listing was accurate but we missed that there isn’t a dishwasher. Parking is a plus!
- Jessica
Adorable Home, Great Town
5/5 stars
Adorable home in a great town. Easy walk to the beaches, parks, and restaurants. Easy access to Salem and Boston (took the T from the Wonderland station) for those seeking activities outside of Marblehead. Owner was very accommodating. Marblehead was a great area and will be spending more time in New England.
- Tom
Sweet retreat indeed
5/5 stars
This was our 3rd stay at sweet retreat!! We just love it!!
- Carol
5/5 stars
Even in the dead of winter, it is cozy and delightful to be in the center of Marblehead!
- Kyra
Nice & easy
5/5 stars
Location is ideal walking distance for to downtown & basics for our stay. The owner was helpful & pleasant to communicate with.
- Justin
Halloween Getaway
4/5 stars
The unit was lovely and exceptionally clean the 4 stars is due to this being advertised as being able to accommodate 5-6 people and it really is not. One of our guests had to sleep on the pull out in the Livingroom and it was quite uncomfortable. We did locate an air mattress however no pump to inflate the mattress. The only other con is the lock mechanisms for the doors are quite tricky and did not lock a few times without the right combination of pulling on the door. The one bathroom was actually not as big of a problem as we thought it would be for five adults just a bit of pre planning and no issue! Aside from that the stay was lovely, we rented a car and the location made it easy to explore Marblehead (amazing little town), Salem (just so much fun on Halloween) and Boston. There are plenty of restaurants within walking distance, the ocean is also walking distance. We recommend the Three Cods right next door. Thanks for the stay!
- Jeannette
5/5 stars
Accommodations were as described, including narrow driveway, but everything was excellent. Location was great with dining and attractions nearby and only a short drive to Salem. Would certainly recommend this to others.
- David
Sweet retreat indeed
5/5 stars
We love this house, so cozy. Great area , walking distance to Restaurants and Salem is 10 minutes drive. This is our second stay. We will be back!
- Carol
MHD family vacation
5/5 stars
We had a great visit. Marblehead is a lovely town and this home was a great location. The driveway is very narrow, making us think twice before we parked the mini van. We had no problems and truly enjoyed our stay. Owners were very friendly, welcoming with helpful info. Thank you!
- Amy
Charming and Great Location
5/5 stars
We spent four delightful nights at Sweet Retreat. The condo was refresh, modern and had everything we needed for our stay. Great access within walking distance to many restaurants, old town and the beach. Also had a chance to meet the owner at her shop on the first floor. Very lovely! Will book again on our next New England adventure.
- Linda
Convenient and comfortable
3/5 stars
Our family stayed here for a week and a half. The washer and dryer were a godsend, since we were traveling with two kids under five. The beds were very comfortable, and the space was bright and sunny. The bar next door was really loud at closing time, so if you travel with little kids, put them in the back bedroom. There was also more furniture than what’s pictured, so there was less room for everyone to spread out to color and play on rainy days. The couches were very uncomfortable (and there was some old popcorn in them, which my kid discovered). There’s also really limited storage for groceries, and the kitchen tools could use some attention (dull knives, no peeler, but five sets of dishes and stemware with gold leaf). There was also no pack n play. For adults looking for a place to sleep during a stay with lots of planned excursions, this apartment would be just fine. For a family, while we enjoyed our stay, we felt the main living space was cramped, cluttered, and noisy.
- Anastasia
Great stay!
5/5 stars
In between homes and the host was very patient and accommodating!
- Linda
Sweet retreat
5/5 stars
Great location, beautiful place, great price, wonderful neighborhood, lots of amenities.
- Jimmy
Great stay
5/5 stars
Very comfortable for our family of 5, clean and well kept.
- Aishlinn
This retreat really is sweet!
5/5 stars
Comfortable, clean and comfortable home in a very convenient location.
- Tere
Sweet Retreat review
3/5 stars
Nice new property center of town next to the Three Cod bar and grill. Well equipped. Driveway is tight coming and going. 2 flights of stairs keep you in shape.
- Michael
Most convenient lodgings EVER!
5/5 stars
We were thrilled to find that everything we wanted or needed was easily within walking distance of this cozy and immaculate lodging during our getaway weekend. The renovations done to the building by the owner are high end. Right next door is a family friendly pub with excellent food. Also close by are several pizza places, many wonderful restaurants serving delicious meals from breakfast to lunch to dinner, a convenient liquor store and pharmacy, historic sites including the fort, many local stores for fun shopping, and more. We didn't set foot in our vehicle until it was time to check out. The location is superb!
- Kathryn
Sweet retreat
5/5 stars
Beautiful home , everything is near by walking distance. Great restaurants. Beautiful area. Had a great time!!!
- Carol
5/5 stars
Loved this getaway! Beautiful accommodations and beautiful town!! Would love to stay again!!!! Very happy with our time spent!
- Erica
Marblehead vacation
5/5 stars
Best location and very clean! We had the absolute best experience staying here!
- Kelsey
5/5 stars
Sweet Retreat is indeed VERY sweet! Amazing how the home, originally built in 1759, was totally renovated to be incredibly comfortable and inviting. The mix of antiques and newer furniture such as the beds was perfect! And the location? Couldn't ask for better, as we literally were able to access numerous excellent restaurants in just a block or two. Marblehead is a GREAT little town on the ocean to relax and unwind. Next time we visit Marblehead, we absolutely, without a doubt, will stay at Sweet Retreat.
- Allan Warren -
Great stay
5/5 stars
Lovely apartment. Everything was terrific.
- Alfred
A wonderful retreat
5/5 stars
Sparking clean, comfortable and has easy access to down town amenities.
- Valerie

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Contact Manager

Phone (978) 737-7084