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Holiday houses in Pleasure Bay

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Top-rated holiday 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.

4 – 11 Jan

$1,701 AUD total

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

29 Dec – 5 Jan

$1,349 AUD total

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.

8 – 15 Apr

$1,805 AUD total

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.

13 – 20 Oct

$1,425 AUD total

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!

21 – 28 Jan

$5,030 AUD total

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

20 – 27 Mar

$1,659 AUD total

Guest favourite

Guest suite in Watertown

4.91 out of 5 average rating, 264 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.

5 – 12 Dec

$1,175 AUD total

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.

24 – 31 Jan

$1,302 AUD total

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.

9 – 16 Aug

$1,480 AUD total

Guest favourite

Guest suite in Winthrop

4.95 out of 5 average rating, 795 reviews

Get to The Point, Winthrop

The Boston Skyline sunsets are beautiful during the summer, just a minute down the street from your Airbnb. This cozy one bedroom, private entrance, and bathroom includes FREE off-street parking, high-speed internet access, comfy and cozy queen bed with premium linens, nespresso, fridge, with complimentary munchies and NO cleaning fee. Check out the beaches and restaurants. Relax watching your favorite show on the HD smart television or catch up on work with the spacious desk area.

11 – 18 June

$2,105 AUD total

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

9 – 16 Oct

$2,463 AUD total

Guest favourite

Home in Boston

4.89 out of 5 average rating, 295 reviews

Treetop Haven in the City

Our space is unique in that it's completely private, affordable, quiet, clean, and with all the amenities you would find in a regular home. It is also cozy, not fancy, but homey. Think of a place you would find in a relative's home. The deck is special - it looks over our neighbor's backyards with plenty of sun and flowers in the Spring and summer. The neighborhood is quiet and safe. No animals are permitted.

28 Dec – 4 Jan

$1,663 AUD total

Holiday rentals for every style

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Popular amenities for Pleasure Bay holiday rentals

Free parking on premises

Air conditioning

Other great holiday rentals in Pleasure Bay

Guest favourite

Guest suite in Newton

4.97 out of 5 average rating, 556 reviews

Spacious suite with private entrance, parking spot

12 – 19 Aug

$1,760 AUD total

Guest favourite

Guest suite in Medford

4.92 out of 5 average rating, 125 reviews

Beautiful 1 Bedroom, 1 Bathroom in Medford

25 July – 1 Aug

$1,594 AUD total

Guest favourite

Apartment in Boston

4.88 out of 5 average rating, 491 reviews

Serene Studio in a Perfect Location

10 – 17 Oct

$2,133 AUD total

Guest favourite

Apartment in Waltham

4.98 out of 5 average rating, 209 reviews

Cozy Private Studio Unit w/ Laundry and Parking!

13 – 20 Jan

$1,588 AUD total

Guest favourite

Apartment in Cambridge

4.94 out of 5 average rating, 318 reviews

private studio near Harvard/MIT

17 – 24 Nov

$2,138 AUD total

Guest favourite

Guest suite in Boston

4.93 out of 5 average rating, 285 reviews

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

24 June – 1 July

$1,787 AUD total

Guest favourite

Home in Boston

4.92 out of 5 average rating, 333 reviews

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

7 – 14 Jan

$3,985 AUD total

Guest favourite

Guest suite in Dover

4.98 out of 5 average rating, 182 reviews

Peaceful Country Home, Dover, Ma: Private Entrance

11 – 18 Mar

$1,776 AUD total

Destinations to explore