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Vacation rentals in Pleasure Bay

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Top-rated vacation rentals in Pleasure Bay

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, 251 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.

Feb. 24 – Mar. 3

$221 CAD per night

Guest favourite

Guest suite in Winchester

5.0 out of 5 average rating, 104 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

Jan. 14 – 21

$147 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.

Jan. 24 – 31

$231 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. 13 – 20

$182 CAD per night

Guest favourite

Home in Boston

4.92 out of 5 average rating, 205 reviews

Sunny Duplex Condo + Private Parking

Welcome to your cozy urban retreat! This 2-bedroom condo, spread over two floors, offers a warm and inviting atmosphere, along with a roof deck offering views of the Boston Harbor waterfront and downtown skyline. And, enjoy the convenience of your very own private parking space! Located just a mile from the vibrant Seaport District, the Boston Convention & Exhibition Center, and major highways, exploring the city couldn't be easier. Experience the warmth and charm of Boston living like a local!

Feb. 21 – 28

$643 CAD per night

Guest favourite

Guest suite in Revere

4.92 out of 5 average rating, 199 reviews

Private Studio 10 min from airport

Private guest suite is centrally-located for easy access to the city. Professionally cleaned. You’ll have a private entrance to come and go as you’d like with a code keypad door. Our newly renovated BASEMENT 500 sq ft is perfect for a guests to escape for a few days. Private bathroom and kitchenette, 10 min away from airport. Bus and train station walking distance. 15 min walk to Revere Beach We are in close proximity to Downtown Boston as well as Salem and other areas. Free wifi Street parking

Feb. 6 – 13

$211 CAD per night

Guest favourite

Guest suite in Watertown

4.91 out of 5 average rating, 265 reviews

Private 1BR Pied-a-terre

Fully furnished mini-suite with private entrance; walk in at ground level. Picture window view of, and use of, large back yard. Separate sitting and sleeping areas (full size bed), desk/workspace, bathroom with shower, kitchenette with small fridge, coffeemaker and microwave (no stove). Great take-out nearby. No pets, no smoking permitted. Car? There is off-street covered parkling. No car? 71 Bus to Harvard Square stops at our corner; short walk to other buses and public transportation.

Nov. 14 – 21

$150 CAD per night

Home in Revere

4.79 out of 5 average rating, 139 reviews

Renovated Cozy City Getaway

Newly renovated cozy 1 bedroom home located on the hills of Beachmont, walking distance from the MBTA train station and Revere Beach. Enjoy sitting on the deck overlooking the Belle Isle Marsh Reservation and Boston Logan Airport in the distance. Take a walk along the beach or take the train into Boston. The location is a 5-10 minute ride to the Airport and a 15 minute train ride to downtown Boston. The unit has new furnishings (2021), modern appliances, and is beautifully decorated.

Jan. 9 – 16

$166 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.

Aug. 12 – 19

$189 CAD per night

Guest favourite

Guest suite in Boston

4.97 out of 5 average rating, 441 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. 15 – 22

$315 CAD per night

Guest favourite

Guest suite in Medford

4.92 out of 5 average rating, 125 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.

Dec. 4 – 11

$193 CAD per night

Condo in Boston

4.82 out of 5 average rating, 177 reviews

Stylish garden level studio with a private patio

Enjoy your stay in this stylish East Boston garden level studio with a private back patio. It is centrally located near restaurants, the waterfront, a running & biking trail, the airport, public transportation, and it is 1 metro stop away from downtown Boston. The metro stop, Maverick, is a 4 minute walk! The studio is equipped with a king bed that has a memory foam mattress, a queen pull out sofa, and a fully equipped kitchen.

Jan. 24 – 31

$234 CAD per night

Vacation rentals for every style

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Popular amenities for Pleasure Bay vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Pleasure Bay

Guest favourite

Home in Boston

4.89 out of 5 average rating, 295 reviews

Treetop Haven in the City

Dec. 28 – Jan. 4

$213 CAD per night

Guest favourite

Apartment in Waltham

4.98 out of 5 average rating, 209 reviews

Cozy Private Studio Unit w/ Laundry and Parking!

Dec. 21 – 28

$203 CAD per night

Guest favourite

Home in Boston

4.92 out of 5 average rating, 333 reviews

3 BR Private Family Home, S. Boston/Seaport/BCEC

Jan. 9 – 16

$533 CAD per night

Guest favourite

Guest suite in Nahant

4.98 out of 5 average rating, 339 reviews

The Annex Oceanfront

Feb. 10 – 17

$235 CAD per night

Guest favourite

Guest suite in Dover

4.98 out of 5 average rating, 182 reviews

Peaceful Country Home, Dover, Ma: Private Entrance

Sep. 18 – 25

$227 CAD per night

Guest favourite

Apartment in Cambridge

4.94 out of 5 average rating, 319 reviews

private studio near Harvard/MIT

Dec. 27 – Jan. 3

$273 CAD per night

Guest favourite

Apartment in Boston

4.88 out of 5 average rating, 493 reviews

Serene Studio in a Perfect Location

Oct. 9 – 16

$273 CAD per night

Guest favourite

Guest suite in Boston

4.93 out of 5 average rating, 285 reviews

Washer+Dryer+Parking!*Private suite*Cul de sac*

Jun. 24 – Jul. 1

$229 CAD per night

Destinations to explore