Winthrop vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

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, 275 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.

Mar 24 – 31

G$42,836 GYD per night

Guest favorite

Cottage in Winthrop

4.99 out of 5 average rating, 418 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.

Jun 24 – Jul 1

G$51,123 GYD per night

Guest favorite

Guest suite in Winchester

5.0 out of 5 average rating, 104 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

Jan 14 – 21

G$21,002 GYD per night

Guest favorite

Condo in Winthrop

4.99 out of 5 average rating, 125 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

Dec 13 – 20

G$54,455 GYD per night

Guest favorite

Guest suite in Winthrop

4.92 out of 5 average rating, 1195 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.

Oct 18 – 25

G$42,966 GYD per night

Guest favorite

Guest suite in Revere

4.93 out of 5 average rating, 200 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

Feb 6 – 13

G$25,525 GYD per night

Superhost

Home in Revere

4.79 out of 5 average rating, 139 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.

Jan 9 – 16

G$20,292 GYD per night

Guest favorite

Apartment in Revere

4.96 out of 5 average rating, 160 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.

Jan 30 – Feb 6

G$40,724 GYD per night

Guest favorite

Guest suite in Nahant

4.98 out of 5 average rating, 339 reviews

The Annex Oceanfront

The Annex is the walk-in cellar apartment of a private home, with neighboring houses close-by. It has its own entrance, with a cemented patio which is part of the seawall. My daughter and I share the house, so it is owner-occupied...along with her dog, Luigi. Although there isn't a stove in the unit, there is a neighborhood restaurant. We are located 30 minutes from Boston. Off street parking is available for one car only. Prices are based on 2 guests. Minimum stay is four nights.

Feb 10 – 17

G$31,791 GYD per night

Guest favorite

Apartment in Winthrop

4.95 out of 5 average rating, 193 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.

Apr 22 – 29

G$57,246 GYD per night

Guest favorite

Guest suite in Winthrop

4.95 out of 5 average rating, 798 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.

Jul 16 – 23

G$48,201 GYD per night

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.

Aug 11 – 18

G$24,869 GYD per night

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

Superhost

Apartment in Revere

4.87 out of 5 average rating, 262 reviews

Beachside Cozy Space-Near Boston/Airport/Train

Jan 30 – Feb 6

G$25,525 GYD per night

Guest favorite

Guest suite in Norwell

4.95 out of 5 average rating, 260 reviews

Private suite South Shore

Oct 7 – 14

G$25,772 GYD per night

Guest favorite

Home in Revere

4.93 out of 5 average rating, 145 reviews

Brand new construction beach unit 🏖🌅⛵🚣🚤🌞🌊🏊

May 4 – 11

G$35,698 GYD per night

Guest favorite

Guest suite in Revere

4.85 out of 5 average rating, 133 reviews

Adorable studio with pool

Feb 2 – 9

G$24,232 GYD per night

Guest favorite

Guest suite in Watertown

4.91 out of 5 average rating, 265 reviews

Private 1BR Pied-a-terre

Jan 3 – 10

G$19,898 GYD per night

Guest favorite

Loft in Swampscott

4.99 out of 5 average rating, 254 reviews

Gorgeous Oceanfront Penthouse

Nov 14 – 21

G$50,652 GYD per night

Guest favorite

Apartment in Marblehead

4.95 out of 5 average rating, 239 reviews

Mid Town Marblehead 1 B/R Pvt. Wing w/Own Entrance

Jan 8 – 15

G$32,723 GYD per night

Guest favorite

Home in Quincy

4.96 out of 5 average rating, 124 reviews

Artist's Haven (2)

Jun 18 – 25

G$24,127 GYD per night

Show all

Other great vacation rentals in Winthrop

Guest favorite

Guest suite in Arlington

4.92 out of 5 average rating, 196 reviews

Modern and comfortable studio apartment

Dec 12 – 19

G$22,796 GYD per night

Superhost

Place to stay in Boston

4.78 out of 5 average rating, 192 reviews

Lovely Private Studio near Logan Airport

Sep 16 – 23

G$35,970 GYD per night

Guest favorite

Apartment in Woburn

4.94 out of 5 average rating, 107 reviews

Comfy-Spacious-private 1BR conveniently located

Jan 16 – 23

G$28,007 GYD per night

Guest favorite

Apartment in Waltham

4.98 out of 5 average rating, 209 reviews

Cozy Private Studio Unit w/ Laundry and Parking!

Dec 21 – 28

G$26,026 GYD per night

Guest favorite

Guest suite in Melrose

4.84 out of 5 average rating, 241 reviews

Guest Suite with separate entrance

Nov 24 – Dec 1

G$25,152 GYD per night

Guest favorite

Guest suite in Peabody

4.94 out of 5 average rating, 196 reviews

Cozy NorthShore Suite Close to SALEM, MA

Jul 18 – 25

G$31,964 GYD per night

Guest favorite

Guest suite in Dover

4.98 out of 5 average rating, 182 reviews

Peaceful Country Home, Dover, Ma: Private Entrance

Sep 18 – 25

G$31,144 GYD per night

Guest favorite

Apartment in Salem

4.97 out of 5 average rating, 301 reviews

The Salem House Too

Dec 12 – 19

G$33,040 GYD per night

Show all

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
G$8,346 GYD 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 2,290 vacation rentals in Orient Heights, over 150 vacation rentals in Beachmont, and over 150 vacation rentals in Cottage Park.
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 apartment rentals in Winthrop have wireless internet?
Absolutely! We offer over 70 apartment rentals with wireless internet in Winthrop. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly apartment rentals in Winthrop?
Winthrop has more than 30 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Condo Rentals in Winthrop?
Enhance your stay in our Condo Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 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 Revere

Guest suite in Norwell

Home in Revere

Guest suite in Revere

Guest suite in Watertown

Loft in Swampscott

Apartment in Marblehead

Home in Quincy

Other great vacation rentals in Winthrop

Guest suite in Arlington

Place to stay in Boston

Apartment in Woburn

Apartment in Waltham

Guest suite in Melrose

Guest suite in Peabody

Guest suite in Dover

Apartment in Salem

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 apartment rentals in Winthrop have wireless internet?

Are there family-friendly apartment rentals in Winthrop?

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

Destinations to explore