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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Guest favorite
A welcoming entryway showcases a wooden staircase leading to the upper levels. The space is enhanced by decorative topiary arrangements and features light-colored flooring providing a bright ambiance. Natural light emanates from a nearby doorway, revealing glimpses of the outdoor area.
Home in Stoughton
4.94 out of 5 average rating, 144 reviews

Modern home 22 min Boston, 20 min Gillette Stadium

Experience New England charm in this luxury home, with over 3,500 sq. feet of living space. This home has many unique characteristics that includes a Koi pond, a majestic backyard and an indoor sauna to make your short term or long term stay more comfortable. It's located in a quiet neighborhood that is walking distance to Glen Echo Park, where hiking, and fishing is available. It's 2 min away from shops, major highways, and has a 6-car driveway and abundance on-street parking. Pet friendly!

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, 115 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
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 spacious yacht is docked along a wooden pier. The boat features a white exterior with a flybridge and is surrounded by calm waters. In the background, other boats and waterfront buildings can be seen under a clear blue sky with a few fluffy clouds.
Boat in Boston
4.95 out of 5 average rating, 148 reviews

2BR Spacious Yacht - Heat & AC- On Freedom Trail

Escape the hustle and bustle of the city and unwind aboard Carpe Diem II, a yacht with 2 comfy queen staterooms for up to 4 adults. Each stateroom has a private bathroom and shower. Unwind on the aft deck with meals and cocktails as the boats sail by on the harbor, or warm up or cool off inside with central A/C and heat. Located in Charlestown Navy Yard, steps to Freedom Trail, North End, and Downtown. Book now and enjoy the unique charm of living on the water in this historic neighborhood.

Top guest favorite
Apartment in Woburn
4.95 out of 5 average rating, 225 reviews

Comfy-Spacious-private 1BR conveniently located

This stylish, private place is perfect for a couple, small family or groups of 4. Just minutes from Boston or the North Shore. Travel by car, Uber, or local train to enjoy Boston excursions, Salem witches, Cape Ann antiquing, sand beaches, fall leaf peeping, skiing, historical sights, sporting events, graduations, and retail therapy at nearby malls, outlets, or ionic Newbury St. A multitude of local and city restaurants and breweries provide an array options for your pleasure. YMCA next door!

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, 216 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, 105 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 modern living area showcases a grey sectional sofa, complemented by a geometric area rug. A small coffee table sits in front, and a desk with a chair is positioned nearby. Large windows provide natural light, and a cityscape photograph adorns the wall.
Apartment in Boston
4.88 out of 5 average rating, 130 reviews

1 BR Gem 5min to Train & Airport explore the city

This modern stylish place to stay is perfect to explore the city of Boston. It’s a hidden gem 1 block away from the Blue Line T station, two stops away from downtown, the aquarium, TD Garden, Faneuil Hall, and multiple museums. 2 mins walking distance from the apartment to Piers Park and spectacular views of Boston Harbor and the skyline.Hop on the ferry to explore Seaport restaurants and bars close by with differing cultures and cuisines. Only 2 min from Logan Airport via train or car.

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 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, 249 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
A well-lit bedroom features a spacious bed with white bedding and decorative pillows. A bedside lamp stands next to the bed, and a window is dressed with long gray curtains. A mirror reflects the room's light, enhancing the sense of openness.
Apartment in Boston
4.89 out of 5 average rating, 183 reviews

Cozy suite in the city!

Enjoy a stylish experience at this centrally-located place in an extremely vibrant neighborhood of Boston. While staying at the AIRBNB, you will be in close proximity to the BCEC if you are in town for work. If you are in town for a pleasure, you will be very close to Downtown Boston, Fenway Park, the Seaport District, Faneuil Hall and the historic North End. You’ll be pleasantly surprised of how easy public transportation is to navigate around the city from the AIRBNB.

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.

Popular amenities for Castle Island vacation rentals

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