Holiday houses in Deer Island

4.87 out of 5 average rating, 68 reviews

Home in Winthrop

Cozy & Modern Entire Residential Home ❤️

Discover your dream stay in this cozy 2bed, 1bath property located in picturesque Winthrop, Ma. It's perfectly situated 5-min from Yirrell Beach offering access to relaxation & city excitement. A convenient 20min drive from the bustling heart of Boston & 15min from Logan Airport & Encore Casino. Walking distance to public transportation & easy access to city adventures. clean & beautifully furnished and has a fully stocked eat-in kitchen, and a spacious deck. Short & long term stays are welcome

4.99 out of 5 average rating, 68 reviews

Condo in Winthrop

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).

4.99 out of 5 average rating, 186 reviews

Condo in Winthrop

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.

4.98 out of 5 average rating, 466 reviews

Cottage in Winthrop

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.

Home in Revere

4.75 out of 5 average rating, 199 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.

4.95 out of 5 average rating, 933 reviews

Guest suite in Winthrop

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.

4.96 out of 5 average rating, 250 reviews

Condo in Boston

CITY APARTMENT NEAR AIRPORT

🏙️ City Apartment Near Airport Station - New Listing! 🏙️ Experience luxury living in this private one-bedroom apartment, ideally situated just one block from the Airport Station. Enjoy easy access to Boston's vibrant attractions, including: Public Library: Just three blocks away, perfect for a quiet afternoon. Bremen's Park: A beautiful green space for relaxation and outdoor activities. Shopping Centers & Trendy Restaurants: Explore a variety of dining and shopping options nearby.

5 out of 5 average rating, 15 reviews

Apartment in Winthrop

Boston Beach Pad Logan Airport

Enjoy the sea breeze & ocean view from your private 2nd floor deck. Located directly across from sandy Winthrop Beach. 2nd floor two bed one bath apartment. 15 Minutes from Logan Airport. 20 minutes to Boston Common. Almost directly next door to Cafe Valenciano Winthrop's only beach front restaurant. Quick walk to Twist & Shake for ice cream & Deer Island Park. Easy access to Salem & the North Shore. Smart projectors fitted with Netflix/streaming services in living room & bedroom

4.97 out of 5 average rating, 63 reviews

Apartment in Winthrop

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.

5 out of 5 average rating, 12 reviews

Apartment in Winthrop

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.

4.86 out of 5 average rating, 118 reviews

Guest suite in Winthrop

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.

5 out of 5 average rating, 19 reviews

Apartment in Everett

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

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Other great holiday rentals in Deer Island

5 out of 5 average rating, 15 reviews

Private room in Lynn

Cozy Private Room

ErinRating, 5 stars3 days ago

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.

4.78 out of 5 average rating, 64 reviews

Private room in Quincy

King Bed w/TV in Spacious Room

KevinRating, 5 stars1 month ago

Excellent place to stay, quiet neighborhood, relatively short distance from Quincy Adams train station. Everything was clean and well organized, check-in instructions were clear. Overall a great experience!

4.82 out of 5 average rating, 68 reviews

Private room in Boston

Boston Charm: Private Room Near Downtown

JelleRating, 5 starstoday

Perfect place to stay! Cosy room upstairs! I was even able to drop off my bagage earlier and the room was already cleaned so i had my room in the morning!

4.9 out of 5 average rating, 10 reviews

Private room in Boston

Private room 3B

NeilRating, 5 stars5 months ago

Very helpful, nice place.

4.92 out of 5 average rating, 79 reviews

Private room in Boston

Cozy Queen Bd, 7mn to Aiport, 3 mn walk to Train

FannyuyRating, 5 stars2 weeks ago

The host is one of the kindest people I have ever met. From feeding me and having a great conversation to giving me a FREE tour of the city, it was a great experience. I have already booked a trip back to Boston just because of this wonderful lady. The room was spotless and it is a great location, less than 5 minutes from the subway. I TOTALLY and ABSOLUTELY recommend!

Hotel room in Chelsea

4.78 out of 5 average rating, 172 reviews

Guest Room with 2 Queen Beds at Chelsea

KyleRating, 5 stars2 weeks ago

Clean, easy to communicate, good amenities including breakfast. Easy and close to everything by car.

4.89 out of 5 average rating, 91 reviews

Private room in Winthrop

Winthrop Home With A View

AnyiethRating, 5 stars3 weeks ago

Lana has been a welcoming host at my time in her apartment. I have never felt bored. She even went a head to suggest some of the incredible sites I should visit in Boston. I strongly recommend her place. There is a peaceful natural environment at Windhrov.