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

Apartment in Winthrop

4.96 out of 5 average rating, 278 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

Cottage in Winthrop

4.99 out of 5 average rating, 423 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

Guest suite in Winchester

5.0 out of 5 average rating, 111 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

Guest suite in Winthrop

4.92 out of 5 average rating, 1206 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

Condo in Winthrop

4.99 out of 5 average rating, 129 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 Revere

4.91 out of 5 average rating, 208 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

Apartment in Woburn

5.0 out of 5 average rating, 100 reviews

Charming 1 BR private entrance apt commuters dream

Newly renovated, spacious 1 B/R apartment. Featuring a private entrance, kitchen with all new stainless-steel appliances, eating/office area, living room and separate bedroom with a Queen-sized bed, streaming cable & WIFI connections, exclusive outdoor space and off-street-parking. Minutes to Rt 95, Rt 128, Rt 93. Easy drive to all major local business, hospitals, mass transportation , airport & commuter rail less than 2 miles. Minutes to Woburn center, Winchester center, shopping & dining.

Superhost

Home in Revere

4.78 out of 5 average rating, 144 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 Salem

4.97 out of 5 average rating, 303 reviews

The Salem House Too

An 1850’s built home with a modern interior and revitalized exterior. It’s the perfect spot to relax and unwind or take work on the road. Located one mile from downtown Salem and away from the traffic, our goal is to provide a classy, upscale experience with all of the comforts of home. Pair a sparkling clean private space with off street parking, unlimited coffee, and a fridge stocked with drinks and snacks and you’ve got The Salem House! Come stay with us and see what Salem is all about!

Guest favorite

Apartment in Winthrop

4.95 out of 5 average rating, 196 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, 809 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

Apartment in Waltham

4.98 out of 5 average rating, 215 reviews

Cozy Private Studio Unit w/ Laundry and Parking!

Superhost

Apartment in Revere

4.86 out of 5 average rating, 158 reviews

Stunning Oceanview-4 Train Stop Logan Airport

Guest favorite

Guest suite in Medford

4.92 out of 5 average rating, 131 reviews

Beautiful 1 Bedroom, 1 Bathroom in Medford

Guest favorite

Guest suite in Norwell

4.95 out of 5 average rating, 262 reviews

Private suite South Shore

Guest favorite

Guest suite in Arlington

4.92 out of 5 average rating, 202 reviews

Modern and comfortable studio apartment

Guest favorite

Guest suite in Scituate

4.91 out of 5 average rating, 177 reviews

Private Scituate Getaway - walk to harbor

Guest favorite

Guest suite in Tyngsborough

4.98 out of 5 average rating, 219 reviews

Lakefront Suite Two-Room, Comfy, Tranquil

Guest favorite

Guest suite in Everett

4.91 out of 5 average rating, 227 reviews

Basement Apartment in prime location near Boston

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Other great vacation rentals in Winthrop

Guest favorite

Apartment in Natick

4.98 out of 5 average rating, 334 reviews

Scandi-Modern Apartment

Guest favorite

Apartment in Salem

4.98 out of 5 average rating, 333 reviews

Historic Salem Willows With Water View

Guest favorite

Guesthouse in Framingham

4.98 out of 5 average rating, 207 reviews

Private guest house on beautiful country road

Superhost

Apartment in Revere

4.88 out of 5 average rating, 265 reviews

Beachside Cozy Space-Near Boston/Airport/Train

Guest favorite

Guest suite in Dover

4.97 out of 5 average rating, 191 reviews

Peaceful Country Home, Dover, Ma: Private Entrance

Guest favorite

Apartment in Everett

4.92 out of 5 average rating, 203 reviews

Huge 1BR w/King Bed near BOS, Salem, Water &Nature

Guest favorite

Guesthouse in Dedham

4.95 out of 5 average rating, 173 reviews

Country Cottage in the City

Guest favorite

Apartment in Cambridge

4.97 out of 5 average rating, 289 reviews

Picture-perfect Cambridge guest apartment, parking

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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 condo rentals in Winthrop?
Experience the best of Winthrop with our condo 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 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 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 condo rentals in Winthrop?
Winthrop has more than 10 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Apartment Rentals in Winthrop?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 60 homes with air conditioning, over 70 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

Apartment in Waltham

Apartment in Revere

Guest suite in Medford

Guest suite in Norwell

Guest suite in Arlington

Guest suite in Scituate

Guest suite in Tyngsborough

Guest suite in Everett

Other great vacation rentals in Winthrop

Apartment in Natick

Apartment in Salem

Guesthouse in Framingham

Apartment in Revere

Guest suite in Dover

Apartment in Everett

Guesthouse in Dedham

Apartment in Cambridge

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 condo rentals in Winthrop?

Do condo rentals in Winthrop have air conditioning?

Do house rentals in Winthrop have wireless internet?

Are there family-friendly condo rentals in Winthrop?

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

Destinations to explore