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Vacation rentals in Thompson Island

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Top-rated vacation rentals in Thompson Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
An inviting living area features a navy blue sofa adorned with two patterned cushions, complemented by a round coffee table. Nearby, a dining set is visible beside a kitchen with stainless steel appliances, wood cabinetry, and ample counter space, illuminated by natural light from a window.
Apartment in Boston
4.99 out of 5 average rating, 116 reviews

Extraordinary 1-Bedroom Apartment in South Boston!

Cozy, comfortable, centrally-located one-bedroom unit in Southie. Unbeatable location, steps from Carson Beach, L Street Bathouse, BCEC, Sail Boston, World Cup 2026! This property presents endless possibilities for creating your perfect getaway! Convenient private entrance ensures hassle-free coming and going. Whether commuting to work, enjoying a concert/game/event/the vibrant local scene, or simply indulging in the beach and parks nearby, you are sure to enjoy it at this very special home!

Top guest favorite
An open living and dining area is highlighted by a wooden dining table set with decorative plates. The space features grey upholstered chairs and a cozy seating arrangement with light-toned furniture. A circular chandelier hangs above, while exposed brick accents add texture to the room.
Apartment in Boston
4.96 out of 5 average rating, 164 reviews

🎖The Ashmont Suite | Close to Subway + Downtown🎖

This high end & unique 3 bed / 2 bath unit is brand new, along with all the furnishings. It includes 1 King, 1 Double, & 1 Single size private bedrooms. The unit is extremely clean and remarkably decorated. Only a 5 minute walk to Ashmont station (red line), which takes you directly into Downtown Boston, Harvard Square, South Boston, Kendall/MIT, U Mass. There’s also plenty of parking available in front of the property. As well as a local coffee shop & a Dunkin just across Ashmont T station.

Top guest favorite
A private deck features comfortable green seating and a glass table, surrounded by colorful potted flowers. Ocean views extend beyond the railing, with trees visible in the background, creating a peaceful outdoor space for relaxation.
Apartment in Nahant
4.94 out of 5 average rating, 160 reviews

Ocean view studio with hot tub & access to Boston

All the amenities needed in a clean, spacious and modern apartment tucked away in a peaceful coastal town close to Boston. Studio with stunning ocean views, large private deck, hot tub, separate entrance, fast internet, granite kitchen, comfy couches, Breville Barista, bbq, and Sealy queen bed. Space is private with quiet residents in adjoining units. Off street parking. 2 sets of stairs to private entry, shared entrance by request. Use of hot tub at no additional cost. Short walk to beaches.

Top guest favorite
A charming yellow Victorian house is framed by lush greenery and tall trees. The front porch features white railings and steps leading to the entrance, with plants adding a welcoming touch. Sunlight softly illuminates the exterior, highlighting the classic architectural details.
Apartment in Dorchester
4.89 out of 5 average rating, 683 reviews

2 bedroom 1st Floor Apartment in Savin Hill

This is a private apartment: living room, one bedroom with a queen size bed and 2 single bed 'Castro Convertibles' and one bedroom with a single bed, bathroom, fully equipped eat in kitchen, back porch and yard. Excellent access to public transportation, downtown area, and tourist attractions. Also suitable for longer stays. One of your hosts is a nurse and we would be happy to host travel nurses. Very convenient to MGH and Longwood Medical area. Please let us know if you are interested.

Top guest favorite
The exterior of a spacious guesthouse showcases a blend of siding and stone finishes. A paved driveway leads to a two-car garage. Lush greenery and flower beds enhance the inviting entrance, while multiple windows allow natural light to fill the interior.
Guest suite in Sharon
4.95 out of 5 average rating, 218 reviews

Cozy Lakeview Guesthouse Near BOS, PVD, Cape Cod

Stunning CLG with private entrance, deck, & parking. •Bedroom #1 ground floor (2 guests only) has a Queen bed & smart TV with deck access. •Bedroom #2 upstairs is ONLY AVAILABLE FOR BOOKINGS OF 3–4 GUESTS and includes a Queen bed, smart TV, mini gym & office. •Living room with lake view & smart TV. •Bathroom with tub and sitting shower bench. •Fully equipped kitchen with stainless steel appliances. •Internet Access, You Tube, and Netflix. •Summer lake access.

Top guest favorite
Condo in Salem
4.95 out of 5 average rating, 106 reviews

The Raven!

Looking for the quintessential Salem stay? Look no further! The main bedroom is designed to get you in the Salem spirit, with its dark gothic decor. Take a reading break in the adjacent room, outfitted to look like a Victorian British library. A spacious living room, dining room, kitchen, and full bath complete this lovely property. Enjoy parking in a driveway in the typically-packed city. We are just a quick and enjoyable 12-minute walk to Essex street and all that downtown has to offer!

Top guest favorite
A spacious living area is shown, featuring a light-colored sectional sofa, an accent chair, and a wooden coffee table. Natural light filters through large sliding doors, which open to a private deck. A soft area rug lies beneath the furniture, enhancing the cozy atmosphere.
Condo in Boston
4.95 out of 5 average rating, 121 reviews

Boston Townhouse - 3BR/2.5BA - Seaport BCEC

Ideal for families with young children, traveling professionals, campus visitors, and tourists! Spacious and recently renovated townhome in South Boston: 3 miles from Logan Airport, 3miles Fenway Park, 2 miles to Seaport, 1 mile to the Boston Convention Center, 1.6 miles to South Station (Commuter Rail/Amtrak), <1 mile to the Red Line (Broadway T-Station) to Kendall Sq (Harvard, MIT) and 1 block from the 9 Bus to Copley (~15min ride to Copley Sq). Great location for World Cup visitors!

Top guest favorite
The exterior of a charming historic home is displayed, featuring pink shingle siding and white trim. Window boxes with flowers and small American flags adorn the windows, creating a festive and welcoming atmosphere, alongside patriotic decorations draped beneath each window.
Guest suite in Boston
4.96 out of 5 average rating, 449 reviews

Paul Revere Suite PVT Entry/BATH QN Bed History

*5 STAR ★★★★★ **No Chores! No To-Do List!** Yes, Private Bathroom! Cleaned and Sanitized *Luxury and Comfort *Historic and charming home. *South Boston trendy neighborhood *Beach two blocks *National Historic Sites *Dedicated Luxury Suites *Key-less Coded Access *Queen Pillow Top Bed *Private bath with shower *Great Bath Amenities *Workstation Free WIFI *Minutes to Airport/Downtown/Convention Center *Netflix Limited street parking. Check the photos for free overnight street parking.

Top guest favorite
A pool table is centrally positioned in the living space, with a selection of colorful billiard balls arranged on its surface. Natural light enters through multiple large windows, illuminating the room. A cozy seating area is visible in the background, with a wood-burning fireplace and decorative shelving.
Apartment in Boston
4.93 out of 5 average rating, 138 reviews

Southie Condo-By Subway-Bring Pets-Pool Table

Spacious 2-bedroom condo in vibrant South Boston’s Andrew Square! Just a 5-minute walk to the Red Line and under 10 minutes to top bars, restaurants, and breweries. Sleeps up to 6 with two cozy bedrooms and a large living room which features a versatile pool table that converts into a ping pong or dining table. Enjoy a full kitchen, fast WiFi, smart TV, and easy access to downtown, the Seaport, and beaches. Perfect for groups, families, or business travelers visiting Boston!

Top guest favorite
A light-filled interior features a wooden dining table positioned near a decorative fireplace. The walls are painted in soft blue, creating a calm setting. A glimpse of a modern kitchen is visible in the background, and a framed artwork adds a touch of character.
Apartment in Boston
4.96 out of 5 average rating, 251 reviews

4br SouthBoston free parkg nrBeach, 6 min>BCEC

Bring the whole family or team -- you'll love our quiet, safe, beachside neighborhood. Our location on the South Boston peninsula means more peace and less traffic, yet a short scenic walk up K Street brings you to great restaurants. <5min walk to a great grocery store, the legendary L St Tavern and L St Bathhouse. <1.5 mi to Convention Center & Seaport. 3 BRs w queen beds and 1 sm BR w bunks, large kitchen, liv & dining rooms, & bonus sunroom w/desk. Call us today -- we'd

Top guest favorite
An open kitchen is paired with a comfortable living area, featuring light hardwood floors. The kitchen includes modern appliances and a spacious island with seating. A neutral-colored sofa and coffee table create a relaxed ambiance, with plants adding a touch of greenery in the background.
Condo in Boston
4.95 out of 5 average rating, 301 reviews

3-Bedroom Apt (7W2) 20-Minuite To Downtown Boston

Perfect for families and groups, this clean, newly renovated 3-level home has 1 King and 2 full size bedrooms and sofa sleeper in living room 2.5 bathrooms (including a half bath on the main floor), and thoughtful touches like snacks, coffee, wine, chargers, travel crib, and fast Wi-Fi. Located in an authentic Boston neighborhood ~20–30 min from downtown by car or transit. Expect lively local character, easy access to public transport, and normal city sounds.

Guest favorite
An airy living space features high ceilings with slanted angles and large windows allowing natural light to filter in. Wooden floors are complemented by simple furnishings, including a dining table with chairs and a bright arrangement of flowers. Nearby, cabinets provide ample storage.
Home in Jamaica Plain, Boston
4.91 out of 5 average rating, 172 reviews

Now availJamaica Plain & Arboretum 20min toBoston

Bright and sunny 2-bedroom retreat with a fully equipped kitchen, spacious bath with rain shower and tub, and TVs in each room. Enjoy fresh coffee daily with espresso maker, milk steamer, and grinder provided. Including a blender..A selection of teas .WiFi and off-street parking included. Private, peaceful, and filled with natural light—perfect for relaxing mornings and cozy evenings!

Popular amenities for Thompson Island vacation rentals

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Suffolk County
  5. Boston
  6. Thompson Island