Holiday houses in Deer Island

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Top-rated holiday rentals in Deer Island

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Guest favourite

Private room in Boston

4.9 out of 5 average rating, 780 reviews

★ Chic, Clean & Large ★ Professionally Cleaned! ★

Need a safe, clean, and comfortable place to stay? You’ve found it. Yes, we are currently hosting guests. You can book for a short or extended stay. PROFESSIONALLY CLEANED AND SANITIZED regularly. Our housekeepers are taking extra care to disinfect frequently touched surfaces between reservations. • MODERN, ULTRA-CLEAN WITH A TON OF SUNLIGHT • JUST 2 SUBWAY STOPS AWAY FROM DOWNTOWN • ULTRA COMFY, LUXURY BED • PRIVATE ROOM WITH LOCK & KEY • AVAILABLE STREET PARKING • 5 MINS TO AIRPORT BY UBER

Guest favourite

Apartment in Quincy

4.88 out of 5 average rating, 8 reviews

Cozy KING BED Suite in Greater Boston Area

ROOF TOP LEVEL Entire Private Apt Suite in Beach City ❀ One Bedroom, One bath ❀ with: ♡ Only about 25min to Harvard Square, MIT, Freedom Trails, Boston Garden, Boston Harbor. A truly convenient location ♡ FREE 01 reserved PARKING space on our parking lot and additional free overnight street parking. ♡ Private Kitchenette ♡ MINUTES DRIVE TO ALL THE NEARBY BEACHES ♡ Countless of dining, hiking, shopping options, everyday eateries are within walking distant ♡ Minutes drive to Quincy Center Station

Top Guest favourite

Condo in Winthrop

4.99 out of 5 average rating, 68 reviews

The Day-Burrill-Wadsworth-La Voix House

The Day-Burrill-Wadsworth-La Voix House is located in Winthrop, MA in the North Shore of Boston. Super close to Logan Airport for your traveling needs. A Level 2 EV Charger is available! This renovated 3 Bedroom penthouse apartment features a private roof deck, off-street parking, sunroom, and free in-unit laundry! A safe, spacious, and serene space. A historic building, it was one of the first handful of homes in Winthrop... built in 1860 (but since converted to two apartments and renovated).

Top Guest favourite

Condo in Winthrop

4.99 out of 5 average rating, 186 reviews

Truly Ocean-Front!: Spacious Family Home + Pets

Truly ocean-front! Don’t be fooled by Winthrop listings of side-street homes. This is an entire 1st floor unit with a private entrance. In an owner-hosted, classic triple-decker home with normal family/town sounds. Pro-cleaned and pet-friendly. Adjacent to Boston by car, ferry/transit. Family time with everything you need. Enjoy our rocky beach or walk a few blocks north to the sandy, lifeguarded stretch. Cafés and restaurants are walkable, and groceries deliver. Quiet hrs: 10pm-7am for all.

Top Guest favourite

Cottage in Winthrop

4.98 out of 5 average rating, 466 reviews

J&K's BnB .... Private studio Airbnb with parking

Our non-smoking private Studio Bnb is located by the airport in Point Shirley; a small safe seaside community. Daily continental breakfast is provided. No cooking allowed, kitchenette with a microwave, coffee maker, a refrigerator. Private bathroom with corner shower, free 5G wireless WiFi, RokuTV, one car off-street parking. Due to our severe medical health allergies to animal hair, fur & feathers, Airbnb has granted us an exemption not to host guests service or emotional support animals.

Top Guest favourite

Apartment in Dorchester

4.89 out of 5 average rating, 676 reviews

2 bedroom 1st Floor Apartment in Savin Hill

This is a private apartment: living room, one bedroom with a queen size bed and 2 single bed 'Castro Convertibles' and one bedroom with a single bed, bathroom, fully equipped eat in kitchen, back porch and yard. Excellent access to public transportation, downtown area, and tourist attractions. Also suitable for longer stays. One of your hosts is a nurse and we would be happy to host travel nurses. Very convenient to MGH and Longwood Medical area. Please let us know if you are interested.

Guest favourite

Guest suite in Winthrop

4.95 out of 5 average rating, 933 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.

Top Guest favourite

Apartment in Winthrop

4.97 out of 5 average rating, 62 reviews

Pleasant Place 2

This stylish place to stay is perfect for a single person or couple. It is a very beautiful space in a lovely 2 family, owner occupied home. Winthrop is a beautiful oceanside residential community situated at the entrance of the most beautiful harbors in New England. Winthrop offers small town suburban living, within minutes to Boston. We have public transportation to downtown Boston in about 20 minutes, Logan Airport in 15 minutes. We also have a Ferry Service to Boston.

Top Guest favourite

Apartment in Winthrop

5 out of 5 average rating, 10 reviews

Boston in 15 Mins!

Stylish 1BR Near Logan & Ocean This stylish 1-bedroom apartment in Winthrop offers the best of both worlds—peaceful coastal charm and quick city access. Key Features: • 15 mins to Logan Airport, 15 mins to Boston • Steps from the beach & scenic harbor views • Modern & cozy space. • Easy access to public transit & ride-shares • Walk to local cafés & restaurants. Whether you’re here for business or a relaxing retreat by the water, this is the perfect spot.

Superhost

Guest suite in Winthrop

4.86 out of 5 average rating, 118 reviews

The Strand on the Beach

Welcome to the 129 The Strand! This accommodation will transport you to a tropical paradise where you can relax and enjoy the sun, sand and sea. Located a few steps from the beach, our Airbnb is the perfect place for your dream vacation. The interior is decorated in a modern and cozy style, and is equipped with everything you need for a comfortable and relaxed stay, it has 1 bed, 1 bath, living room, private entrance, parking, & refrigerator.

Guest favourite

Apartment in Everett

5 out of 5 average rating, 17 reviews

Elegant Oasis with Pool and Gym

Discover your exclusive retreat in Everett. Immerse yourself in sleek, curated living with designer finishes and resort‑style amenities for an unforgettable stay. Highlights: • Steps from downtown Boston via easy Silver Line & Route 1 access • Sparkling pool with cabana seating and courtyard fire pits • 24/7 state‑of‑the‑art fitness center & dedicated yoga studio • Private music room, co‑working pods & on‑site community pet spa

Top Guest favourite

Private room in Winthrop

4.95 out of 5 average rating, 354 reviews

Shirley's Sea Breeze airport getaway 2 single beds

Our home is nestled in this charming seaside neighborhood close to Boston Logan Airport and close to down town Boston. We are delighted to be able to offer you a spacious private bedroom and access to our home. You’ll share my home with me (Shirley) and my two cats, Caleb and Otto. Come enjoy the front porch or back deck and take in the Salty air and harbor breeze we would be delighted to host you

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Popular amenities for Deer Island holiday rentals

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Other great holiday rentals in Deer Island

Guest favourite

Private room in Boston

4.93 out of 5 average rating, 15 reviews

Modern Home - w/ Comfort Amenities

AlexandriaRating, 5 stars2 weeks ago

this is a wonderful place to stay and Alix is such a great host! can't wait to stay here again :)

Top Guest favourite

Private room in Lynn

5 out of 5 average rating, 15 reviews

Cozy Private Room

ErinRating, 5 starstoday

I loved staying here. Phuong is kind and welcoming, and her dog is a great co-host. Bed is very comfortable and room darkening shades were available. Would definitely stay here again.

Private room in Boston

4.67 out of 5 average rating, 311 reviews

The Jazzy Airbnb

JinyoungRating, 5 stars2 weeks ago

I really enjoyed the stay. I stayed here to catch the transportation from the south station the next day. The room was clean and well maintained, although a bit old, although it was a bit difficult to move the suitcases as the room was located on the second floor. The neighborhood felt quiet and safe while walking 10 minutes from the metro station. The hosts are very friendly, responsive and do their best to help.

Hotel room in Chelsea

4.78 out of 5 average rating, 169 reviews

Guest Room with 2 Queen Beds at Chelsea

AdrianaRating, 5 stars2 weeks ago

We only stayed for one night but our experience was excellent, very comfortable and the staff is very helpful. Will be back!

Guest favourite

Private room in Quincy

5 out of 5 average rating, 12 reviews

Priv Bdrm W. Quincy/ E. Milton

ElsaRating, 5 stars3 days ago

Didn’t get a chance to cross paths with William but he’s a great host! Very responsive and proactive. He was super nice and helpful from the get go. Had an issue with the shower drain and he attended to it immediately after I messaged him. His place was clean, and just as described and pictured. Made you feel right at home! I did appreciate his personal touch in the room : he left a little handy book with recommendations on what to eat, where to shop and how to get around the city. I thought that was very thoughtful of him! Would recommend 9.5/10. Be mindful if you don’t like cats as he has a big cat for a pet.

Guest favourite