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Vacation rentals in Thimble Island

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Top-rated vacation rentals in Thimble Island

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

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Apartment in Boston

4.89 out of 5 average rating, 254 reviews

🎖The Boiler Room | Close to Subway + Downtown🎖

This unique private suite is brand new & comes w/ its own private entrance. Including a queen size bed, ensuite bathroom, & a wine/craft beer minibar! The unit is extremely clean and very nicely decorated. A quick 5 minute walk to Ashmont Station (Red Line), which takes you directly into Downtown Boston, Harvard Square, South Boston, Kendall/MIT, U Mass. Great restaurants nearby - Molinari's & Tavolo Ristorante - as well as a local coffee shop + a Dunkin just across the Ashmont metro station.

Apr. 4 – 11

$227 CAD per night

Guest favourite

Guest suite in Boston

4.96 out of 5 average rating, 203 reviews

Upscale 2 Bdrm Suite: Kitchen, Spa Bath, Laundry

The home is a short 7 minute walk to Ashmont T Stop. A truly unique master bedroom and a cozy 2nd bedroom both adjacent to a marble spa bathroom (which has a heated floor and a large shower with a built in bench). With a clean, glass-tiled kitchen with granite-top counters, you'll be staying in a nice deluxe suite that is set in a friendly, safe neighborhood perfect for romantic couples, solo adventurers, and savvy business travelers who want the feel of a downtown hotel without the high price.

Nov. 28 – Dec. 5

$232 CAD per night

Guest favourite

Guest suite in Winchester

5.0 out of 5 average rating, 106 reviews

Warm and cozy 1st flr sweet guest suite w parking

Easy living at this peaceful and centrally-located guest suite. Winchester is the quintessential New England town located just 8 miles from Boston with an easy drive or 16 minute by train from Winchester Center or Wedgemere. Or check out historic Lexington and Concord next door, bustling Arlington Center or hip Davis Square. Tufts University, Harvard Square, Harvard University and MIT nearby. Your comfortable home away from home for fun excursions, get aways, business meeting or college visits

Dec. 2 – 9

$184 CAD per night

Guest favourite

Apartment in Waltham

4.98 out of 5 average rating, 210 reviews

Cozy Private Studio Unit w/ Laundry and Parking!

Almost every guest describes my place as cozy, which was the feeling I was going for when I designed the space! You will love this large 400 sq. ft private 1 bedroom studio. This unit has a private entrance w/ punch code door, full bathroom, large walk-in closet, mini fridge, freezer and microwave. It has one parking spot in the driveway and a washer /dryer. The backyard is shared but the unit has a private patio. Rental is attached to a single family home. (Please note: No full kitchen)

Dec. 4 – 11

$204 CAD per night

Guest favourite

Guest suite in Boston

4.91 out of 5 average rating, 196 reviews

Cozy Private Garden Studio near the Heart of JP

Best of both worlds: this airy and light, newly renovated private studio is set in a beautiful, secluded backyard/garden. Easy walk to restaurants, shops and acres of green space. Your reservation confirms that you have read "Other Things to Note" in The Space section below and "House Rules" before booking. Guests can only book for themselves. We are 5-7 minutes from the 39 bus and 15 from the Orange line. There is a microwave, fridge, counter and and sink but no stove or cooking options.

Oct. 26 – Nov. 2

$183 CAD per night

Guest favourite

Guest suite in Dover

4.98 out of 5 average rating, 184 reviews

Peaceful Country Home, Dover, Ma: Private Entrance

Graceful country oasis in a renovated 125 year old historic home, 35 minutes driving time from downtown Boston. (Important-stairs climbing required to reach bedroom suite.) I welcome quiet, mature guests. We are located on a scenic road in sophisticated Dover, Ma, a commuter/country setting, with miles of hiking trails and roads ideal for cycling, and surprisingly close to downtown Boston. I have owned and loved this home for 33 years and take great joy in its charm and outdoor spaces.

Jan. 6 – 13

$228 CAD per night

Guest favourite

Guest suite in Peabody

4.98 out of 5 average rating, 177 reviews

Cozy West Peabody Guest Suite

Come enjoy this renovated studio guest suite in the quiet neighborhood of West Peabody! An easy drive to Salem or Boston, close to a woodsy bike trail, and a short drive to local shops and restaurants. Features a fully equipped kitchenette and an outdoor space with a fire pit and charcoal grill. Make use of a Roku TV and fast, reliable WiFi to keep yourself entertained. This is a great space whether you are looking to explore the Boston North Shore or simply embark on a quiet getaway.

Oct. 28 – Nov. 4

$227 CAD per night

Guest favourite

Home in Boston

4.89 out of 5 average rating, 296 reviews

Treetop Haven in the City

This is a sweet, cozy space that is not fancy but homey. You will have everything you need for a comfortable stay including a complete kitchen with everything you will need to make your own meals. We are conveniently located, near the subway and buses, supermarkets, restaurants, and coffee shops. We are within two blocks of the jewel of the Emerald Necklace, Jamaica Pond, and other green spaces. Read our reviews so you can see what previous guests have loved about Treetop Haven.

Jul. 4 – 11

$210 CAD per night

Guest favourite

Guest suite in Boston

4.97 out of 5 average rating, 446 reviews

Boston’s Hidden Gem: One by Land Suite

*5 STAR ★★★★★ **No Chores! No To-Do List!** *Sparkling Clean and Sanitized *Yes a Private Bathroom *Historic and charming home. *South Boston trendy neighborhood *Beach two blocks *Dedicated Luxury Suites *Key-less Coded Access *King EuroTop Bed *Private bath with shower *Workstation Free WIFI *Minutes to Airport/Downtown/Convention Center *Netflix Limited street parking. Check the photos for free overnight street parking. Paid parking located at: 12 Drydock Ave, Boston, MA 02210

Oct. 12 – 19

$317 CAD per night

Guest favourite

Guest suite in Medford

4.92 out of 5 average rating, 127 reviews

Beautiful 1 Bedroom, 1 Bathroom in Medford

Come stay in this recently renovated, very comfortable space situated in a quiet neighborhood across the street from the Brooks Estate woods, just outside of Boston. The house itself is a historical gothic cottage built in 1856 and is the 2nd oldest home in the area. The space is in a historic single family home and both the bedroom and bathroom are 100% PRIVATE and separated from the rest of the house with a private entrance.

Aug. 15 – 22

$205 CAD per night

Guest favourite

Home in Quincy

4.96 out of 5 average rating, 124 reviews

Artist's Haven (2)

Before booking, please conduct thorough research on Quincy, MA, to ensure it aligns perfectly with your needs. As a dedicated Superhost, I'm committed to earning your 5-star review. My home offers easy check-in with a keypad entry. The cozy second-floor one-bedroom has a private entrance, spa-like bathroom, well-equipped kitchen, queen-sized bed, 55" TV, high-speed WiFi, and on-site parking for one car.

Jul. 24 – 31

$196 CAD per night

Guest favourite

Apartment in Boston

4.88 out of 5 average rating, 494 reviews

Serene Studio in a Perfect Location

Our 500 sf 2 room apartment is quiet, private & ideally situated in the heart of Jamaica Plain-just a 4 min. walk to the Orange Line subway and buses. It offers a super comfortable bed, and all the necessities-wifi, 4K smart TV, large eat-in kitchen, Nespresso coffee, and free on-street parking.

Oct. 18 – 25

$273 CAD per night

Vacation rentals for every style

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Popular amenities for Thimble Island vacation rentals

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Air conditioning

Other great vacation rentals in Thimble Island

Guest favourite

Guest suite in Brookline

4.88 out of 5 average rating, 186 reviews

Brookline Home with a Garden

Oct. 11 – 18

$238 CAD per night

Guest favourite

Apartment in Boston

4.92 out of 5 average rating, 269 reviews

Apartment 1BR mins from JFK/UMASS on Red Line

Dec. 13 – 20

$317 CAD per night

Apartment in Weymouth

4.81 out of 5 average rating, 167 reviews

Lovely studio on the coast! Beach close by!

Aug. 30 – Sep. 6

$226 CAD per night

Guest favourite

Guest suite in Scituate

4.91 out of 5 average rating, 176 reviews

Private Scituate Getaway - walk to harbor

Sep. 20 – 27

$193 CAD per night

Guest favourite

Guest suite in Revere

4.94 out of 5 average rating, 101 reviews

Corner Cottage - cozy studio just north of Boston

Sep. 7 – 14

$218 CAD per night

Guest favourite

Home in Jamaica Plain

4.93 out of 5 average rating, 127 reviews

Fully-Equipped, Private 1st Floor 1-Bed/1-Bath Apt

Jan. 1 – 8

$317 CAD per night

Home in Revere

4.8 out of 5 average rating, 143 reviews

Renovated Cozy City Getaway

Jan. 14 – 21

$168 CAD per night

Guest favourite

Apartment in Quincy

4.94 out of 5 average rating, 142 reviews

Short Train 2 Boston, Luxury prvt unit w parking

Jan. 18 – 25

$337 CAD per night

Destinations to explore