Winthrop vacation rentals

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Top-rated vacation rentals in Winthrop

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Winthrop

4.99 out of 5 average rating, 420 reviews

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

Our non-smoking private Studio Bnb is located by the airport in a small safe seaside community called Point Shirley. Daily continental breakfast is provided. No cooking allowed, kitchenette with a microwave, coffee maker, a refrigerator. Private bathroom with corner shower, free wireless Wi-Fi, 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.

Guest favorite

Apartment in Winthrop

4.96 out of 5 average rating, 276 reviews

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.

Guest favorite

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

Guest favorite

Condo in Winthrop

4.99 out of 5 average rating, 127 reviews

Beachfront Boston: Large, Cozy, Relaxed + Pets

New 2-person soaker tub with ocean-view! Gather with family & friends in this owner-hosted home. Private entrance, entire 1st floor of a multi-family home, with normal family/kid sounds. Pro-cleaned and pet-friendly, space for everyone. Scoot into adjacent Boston by car, ferry/transit, or snuggle-up for a movie on the 70” TV. 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

Guest favorite

Guest suite in Winthrop

4.92 out of 5 average rating, 1199 reviews

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.

Guest favorite

Guest suite in Revere

4.92 out of 5 average rating, 202 reviews

Private Studio 10 min from airport

Private guest suite is centrally-located for easy access to the city. Professionally cleaned. You’ll have a private entrance to come and go as you’d like with a code keypad door. Our newly renovated BASEMENT 500 sq ft is perfect for a guests to escape for a few days. Private bathroom and kitchenette, 10 min away from airport. Bus and train station walking distance. 15 min walk to Revere Beach We are in close proximity to Downtown Boston as well as Salem and other areas. Free wifi Street parking

Guest favorite

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!

Superhost

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.

Guest favorite

Apartment in Revere

4.96 out of 5 average rating, 162 reviews

Ikram's Place Close to Boston,Subway,Airport,Beach

Our place is located in North of Boston, in a very quite neighborhood , it has a Great Ocean view, free parking in the property, front yard and back yard for barbecue. We offer coffee, milk, Tea, toast, bottled of water, OJ,eggs, waffles etc, Bikes and fishing rods available open request. 1 min walking to the Beach,7 min to the T and 10 min to Downtown Boston via subway. total Privacy in the whole apartment .Our place is good for couples, solo adventurers, business travelers, and families.

Guest favorite

Apartment in Winthrop

4.95 out of 5 average rating, 194 reviews

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. Our saltwater pool is nicely terraced and overlooks stunning ocean views. We are 4 short miles from the city and public transportation is easily accessible; a convenient option into Boston. 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.

Guest favorite

Guest suite in Winthrop

4.95 out of 5 average rating, 802 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.

Guest favorite

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.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Winthrop vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Winthrop's top sights

Deer Island22 locals recommend

Belle Isle Seafood27 locals recommend

Stop & Shop15 locals recommend

Angela's Cafe Orient Heights12 locals recommend

Nick's Place11 locals recommend

Donna's Restaurant12 locals recommend

Other great vacation rentals in Winthrop

Guest favorite

Guest suite in Medford

4.92 out of 5 average rating, 127 reviews

Beautiful 1 Bedroom, 1 Bathroom in Medford

Superhost

Apartment in Revere

4.87 out of 5 average rating, 263 reviews

Beachside Cozy Space-Near Boston/Airport/Train

Guest favorite

Guest suite in Everett

4.91 out of 5 average rating, 221 reviews

Basement Apartment in prime location near Boston

Guest favorite

Apartment in Salem

4.97 out of 5 average rating, 302 reviews

The Salem House Too

Guest favorite

Guest suite in Melrose

4.84 out of 5 average rating, 244 reviews

Guest Suite with separate entrance

Guest favorite

Guest suite in Norwell

4.95 out of 5 average rating, 261 reviews

Private suite South Shore

Guest favorite

Guest suite in Marblehead

4.97 out of 5 average rating, 263 reviews

Private Loft Right on Atlantic Avenue

Guest favorite

Loft in Swampscott

4.99 out of 5 average rating, 256 reviews

Gorgeous Oceanfront Penthouse

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Other great vacation rentals in Winthrop

Guest favorite

Guest suite in Dover

4.98 out of 5 average rating, 184 reviews

Peaceful Country Home, Dover, Ma: Private Entrance

Guest favorite

Guest suite in Marblehead

4.92 out of 5 average rating, 246 reviews

Ocean Park Retreat

Guest favorite

Apartment in Stoneham

4.88 out of 5 average rating, 146 reviews

Entire guest suite in Stoneham

Guest favorite

Apartment in Waltham

4.98 out of 5 average rating, 210 reviews

Cozy Private Studio Unit w/ Laundry and Parking!

Guest favorite

Apartment in Somerville

4.91 out of 5 average rating, 170 reviews

Spacious, private apartment in perfect location

Superhost

Place to stay in Boston

4.78 out of 5 average rating, 192 reviews

Lovely Private Studio near Logan Airport

Guest favorite

Apartment in Revere

4.95 out of 5 average rating, 154 reviews

Quiet Neighborhood Luxury Stay

Guest favorite

Apartment in Winthrop

4.95 out of 5 average rating, 19 reviews

Vibrant Winthrop Apartment - Close to Ocean!

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Quick stats about vacation rentals in Winthrop

Total rentals
150 properties
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
12K reviews
Nightly prices starting at
$40 before taxes and fees

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 150 vacation rentals in Cottage Park, over 150 vacation rentals in Beachmont, and over 2,290 vacation rentals in Orient Heights.
Are there pet-friendly vacation rentals in Winthrop?
Four-legged friends are welcome in Winthrop. Choose from more than 40 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 70 vacation rentals in Winthrop featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in apartment rentals in Winthrop?
Experience the best of Winthrop with our apartment rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Winthrop have air conditioning?
Absolutely! We offer over 60 apartment rentals with air conditioning in Winthrop. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winthrop have wireless internet?
Absolutely! We offer over 40 house rentals with wireless internet in Winthrop. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Winthrop?
Winthrop has more than 10 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 30 homes with air conditioning, over 40 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.

Winthrop vacation rentals

Top-rated vacation rentals in Winthrop

Vacation rentals for every style

Apartments

Houses

Hotels

Popular amenities for Winthrop vacation rentals

Stay near Winthrop's top sights

Other great vacation rentals in Winthrop

Guest suite in Medford

Apartment in Revere

Guest suite in Everett

Apartment in Salem

Guest suite in Melrose

Guest suite in Norwell

Guest suite in Marblehead

Loft in Swampscott

Other great vacation rentals in Winthrop

Guest suite in Dover

Guest suite in Marblehead

Apartment in Stoneham

Apartment in Waltham

Apartment in Somerville

Place to stay in Boston

Apartment in Revere

Apartment in Winthrop

Quick stats about vacation rentals in Winthrop

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Where should I stay in Winthrop?

Are there pet-friendly vacation rentals in Winthrop?

Are there vacation rentals with a dedicated workspace in Winthrop?

How much does it cost to stay in apartment rentals in Winthrop?

Do apartment rentals in Winthrop have air conditioning?

Do house rentals in Winthrop have wireless internet?

Are there family-friendly house rentals in Winthrop?

What are the most popular amenities for House Rentals in Winthrop?

Destinations to explore