
Vacation rentals in Winthrop
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Winthrop
Guests agree: these stays are highly rated for location, cleanliness, and more.

Cody's Place Boston Airport Pool/Beaches ParkFree
Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

Licensed Boston airport studio 5 stars, subway
We are a licensed & permitted Airbnb in the Boston area, ensuring a safe, reliable experience for all our guests, meeting safety & inspectional standards. Flexible early/late check in/out, please advise us of your expected check in and check out times so we can better accommodate you & your travel plans. Normal check in 3pm, normal check out 11am. Please let us know if you need parking, we provide free off street parking during your stay. Window AC in the summer. Looking forward to hosting you.

Oceanfront Pool. Close to Boston. Free Parking.
Enjoy a relaxing & tranquil beach setting while having quick access to Boston and all it has to offer. Stunning ocean views can be seen from our seasonal saltwater pool and all-season hot tub (exclusive during your stay). We are 4 short miles from Boston & public transportation is easily accessible. Winthrop is a welcome relief from the hustle and bustle of the city, where you can come "home" and wind down to the sound of ocean waves, seaside birds, gorgeous sunrises, and beautiful moon rises.

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.

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.

Beachmont Guest Suite
Experience tranquility in our modern guest suite with stunning ocean views and a private deck overlooking the Atlantic. Wake up to breathtaking sunrises and relax by the cozy gas fireplace. Features a fully equipped kitchen with island seating, a comfortable queen bed, a plush sectional couch, and a luxurious bathroom. Just minutes from Boston, enjoy beachfront living—ideal for romantic getaways, peaceful retreats, or business travelers. Book now to experience the best of beachfront living!

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.

Stunning Oceanview-4 Train Stop Logan Airport
Stunning 1 bedroom huge apartment with partial ocean views of Revere Beach. This upscale home has it all!! Just one flight up then you enter a hardwood floor foyer, opens to a huge living room with upscale decor, large eat in kitchen stainless steel appliance, country table has seating for 4, tile floor, gas range, and lots of cabinet space, with views of Revere Beach and ocean, giant bathroom complete with tiled shower and stackable laundry (Washer and Dryer) and huge bedroom with closet.

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.

Cozy studio, near beaches and city skyline views
The Boston Skyline sunsets are beautiful during the summer, just a minute down the street from your Airbnb. This cozy studio, with 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.

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.

Boston 3 Room Apt 5 Min Walk to Train & Beach
Sunny 3 room apartment with private entrance, in 150 year old renovated home. A short walk to Revere Beach and the MBTA Blue Line, be at Logan Airport or Downtown Boston in minutes. The apartment has a full kitchen, spacious bedroom with very comfortable king size bed and TV. The living room has a leather sofa, recliner, desk and TV. Laundry on site. Free Driveway Parking.
Popular amenities for Winthrop vacation rentals
Other great vacation rentals in Winthrop

Sunny 2br appt close to Boston/Airport/Beaches.

Pleasant Place 2

Sea Forever - Oceanfront Home in Nahant!

Cozy & Modern Entire Residential Home ❤️

Charming condo steps from beach

The Day-Burrill-Wadsworth-La Voix House

3 bdr, steps from the ocean, minutes from Boston

Garden Apartment
Quick stats about vacation rentals in Winthrop
Total rentals
190 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
17K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
10 properties have a pool
Frequently Asked Questions
Where should I stay in Winthrop?
Make yourself at home in Winthrop by choosing from our most frequently booked neighborhoods. We have over 200 vacation rentals in Beachmont, over 2,550 vacation rentals in Orient Heights, and over 200 vacation rentals in Point Shirley.
Are there pet-friendly vacation rentals in Winthrop?
Four-legged friends are welcome in Winthrop. Choose from more than 50 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Winthrop?
Yes! Work meets play with ease at over 90 vacation rentals in Winthrop featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Winthrop vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Winthrop, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Winthrop have wifi?
Absolutely! We offer over 60 house rentals with wifi in Winthrop. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in condo rentals in Winthrop?
Experience the best of Winthrop with our condo rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do condo rentals in Winthrop have air conditioning?
Absolutely! We offer over 10 condo rentals with air conditioning in Winthrop. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Winthrop have a gym?
Absolutely! We offer over 10 apartment rentals with a gym in Winthrop. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Winthrop?
Winthrop has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Winthrop?
Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with air conditioning, over 60 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
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