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Vacation rentals in Castle Island

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Top-rated vacation rentals in Castle 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.

Mar 5 – 12

G$25,551 GYD per night

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

Jan 1 – 8

G$26,122 GYD per night

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 25 – Nov 1

G$22,454 GYD per night

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!

Dec 22 – 29

G$81,888 GYD per night

Cabin in Cohasset

4.92 out of 5 average rating, 286 reviews

Lionsgate at Cohasset

Lionsgate is the perfect retreat to refresh the soul. Newly remodeled fully stocked kitchen with comfortable amenities provide a home away from feel. Enjoy a roaring fire in a rustic cabin during the winter or the coolness of a mini split in the summer. Cohasset, jewel of the South Shore is a quintessential New England seaside village located half way between Boston and Cape Cod. The ocean offers abundant recreation opportunities as well as plentiful parks for hiking and biking. A must visit.

Sep 11 – 18

G$29,579 GYD per night

Guest suite in Salem

4.99 out of 5 average rating, 695 reviews

The Mason Suite of Salem

*We have THE BEST location in all of Salem! Take a look at our reviews!* The Mason Suite is a boutique lodging experience with all the comforts of home! Built in 1844 and nestled among Salem's most prized architecture, the Suite is just steps from the Witch Museum, bustle of the pedestrian mall, and Salem Common! Recently renovated from top to bottom! You'll be surrounded by fine furnishings, culture and history! The location is 10/10! We strive to provide you with the ideal Salem experience!

Apr 18 – 25

G$30,424 GYD per night

Home in Revere

4.8 out of 5 average rating, 143 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 14 – 21

G$20,325 GYD per night

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

G$29,741 GYD per night

Guest suite in Revere

4.94 out of 5 average rating, 101 reviews

Corner Cottage - cozy studio just north of Boston

Whether you’re a tourist visiting Boston for the weekend, a traveling nurse in search of a medium-term stay, or a pilot/flight attendant needing overnight accommodations, this completely renovated and professionally cleaned AirBnB is perfect for you! Finding living accommodations is tough; finding a reliable and responsive host is even tougher. Not only is this unit well equipped with almost everything you may need, but I will do my best to ensure your stay is the most comfortable.

Sep 7 – 14

G$27,015 GYD per night

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

G$40,353 GYD per night

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.

Jan 19 – 26

G$23,361 GYD per night

Condo in Boston

4.83 out of 5 average rating, 183 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.

Feb 5 – 12

G$27,418 GYD per night

Vacation rentals for every style

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Popular amenities for Castle Island vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Castle Island

Guest suite in Dover

4.98 out of 5 average rating, 184 reviews

Peaceful Country Home, Dover, Ma: Private Entrance

Dec 8 – 15

G$31,116 GYD per night

Apartment in Waltham

4.98 out of 5 average rating, 210 reviews

Cozy Private Studio Unit w/ Laundry and Parking!

Dec 12 – 19

G$26,003 GYD per night

Guest suite in Revere

4.92 out of 5 average rating, 202 reviews

Private Studio 10 min from airport

Dec 9 – 16

G$25,570 GYD per night

Guest suite in Norwell

4.95 out of 5 average rating, 261 reviews

Private suite South Shore

Sep 19 – 26

G$25,749 GYD per night

Apartment in Dorchester

4.88 out of 5 average rating, 630 reviews

2 bedroom 1st Floor Apartment in Savin Hill

Aug 18 – 25

G$31,423 GYD per night

Home in Boston

4.89 out of 5 average rating, 296 reviews

Treetop Haven in the City

Jul 4 – 11

G$25,508 GYD per night

Apartment in Revere

4.91 out of 5 average rating, 237 reviews

Boston 3 Room Apt 5 Min Walk to Train & Beach

Sep 1 – 8

G$34,641 GYD per night

Apartment in Boston

4.8 out of 5 average rating, 211 reviews

Beacon Hills Studio next to State house 3

Feb 2 – 9

G$28,542 GYD per night

Destinations to explore