
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.

The sweet suite
Ground level. Spacious room with a King Bed and a bonus smroom with a ( twin pull out bed) couch and desk/vanity. The sizeable bathroom is freshly remodeled. Kitchenette has a small sink, refrigerator and microwave. It is in a quiet neighborhood only minutes from a rail trail, route 62, interstate 95 route 1 and route 128. Off Street parking. We are 5 miles to Salem Mass, 44 miles to New Hampshire, 77 miles to the cape cod canal, 19 miles to Boston. We are 4 miles to the Beverly train Station.

Cody’s Place | Boston Area Pool, Beach & Parking
Cody’s Place is a clean, comfortable stay mins from Boston, airport & beach - with heated pool & free parking. Thoughtfully hosted for a smooth, stress-free stay perfect for travelers, couples, or a quick getaway seeking convenience, comfort & prime location Private entry basement directly across from the ocean. Enjoy fresh sea air, sunrises & a restaurant steps away • Steps to beach • Mins to Airport • Boston access (ferry/Uber) • Free on-site parking • Fast WiFi + Smart TV • Easy self check-in

Homey getaway by the beach
Cute and homey well furnished 3 bedroom apartment in an older 2 family beach house. 1 min walk away from the best and least crowded part of Nantasket Beach, and a short 5 min drive from the Hull downtown. Ideal for vacationers, visitors, and families, the house features 3 bedrooms, 2 full baths, a nice and well equip kitchen with quality Samsung appliances, and a small BBQ deck overlooking a private backyard with a picnic table and stone patio. The house is literally 175 Yards from the beach :-)

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.

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.

The Raven!
Looking for the quintessential Salem stay? Look no further! The main bedroom is designed to get you in the Salem spirit, with its dark gothic decor. Take a reading break in the adjacent room, outfitted to look like a Victorian British library. A spacious living room, dining room, kitchen, and full bath complete this lovely property. Enjoy parking in a driveway in the typically-packed city. We are just a quick and enjoyable 12-minute walk to Essex street and all that downtown has to offer!

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.

French Flair "Pied a Terre" Cottage on the Marsh
Sunny cottage with marsh views, under 5 minute walk to town. Eat on the water in one of the many village restaurants, rent a kayak or paddle board. Go "down river" like a local! Shop the world renowned antique stores or enjoy the local beaches. There are many unique places to visit in Gloucester, Manchester, Rockport, Ipswich, Salem and of course Boston. There is a Visitor Manual for your convenience and we would be happy to answer questions that you might have.

Lovely 1 Bedroom Guest House. Downtown Cohasset
Lovely guest house. Newly renovated, nicely furnished & clean. Spacious living room/dining room with fully equipped kitchen. Large 1 bedroom & 2 full baths. Convenient location--walk to downtown, harbor, restaurants, churches and the Common. Train to Boston"s South Station 5 min away. Cohasset is the quintessential New England seaside village located on the South Shore of Massachusetts between Boston and Cape Cod. Host lives next door on property.

Shoreview Studio Lounge
This historic Victorian residence, is today host to this seaside studio lounge. Once inside, you’ll fall captive to the seascape off Independence Park. The Atlantic panorama provides an awe-inspired sunrise daily. From its elevated perch, the studio has a contemporary feel with its private observation deck to its sophisticated lighting and wet bar design. Comforts include heated floors, air conditioning and powered room-darkening blinds.

Oceanfront Penthouse · Kings Beach · Breathtaking
The Loft Wake up to the ocean. This top-floor penthouse sits directly on Kings Beach with unobstructed water views from every window. Cathedral ceilings, skylights, hardwood floors, a quartzite kitchen, and a jetted spa tub make this one of the North Shore’s most distinctive stays. Your own private deck. 28 minutes to Boston by commuter rail — the world is at your door, but you won’t want to leave.
Popular amenities for Winthrop vacation rentals
Other great vacation rentals in Winthrop

Entire 1st floor apt in charming seaside Beverly

Newly Renovated Ocean View 2 Bdrm Apt

Pleasant Place 2

Boston 3 Room Apt 5 Min Walk to Train & Beach

Warm home in Lexington, walk to town, nature trail

Country Cottage in the City

Cozy & Modern Entire Residential Home ❤️

Charming condo steps from beach
When is the best time to visit Winthrop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R2,047 ZAR | R2,131 ZAR | R2,521 ZAR | R2,537 ZAR | R2,808 ZAR | R2,808 ZAR | R2,876 ZAR | R2,994 ZAR | R2,673 ZAR | R2,825 ZAR | R2,453 ZAR | R2,250 ZAR |
| Avg. temp | -1°C | 0°C | 4°C | 9°C | 15°C | 20°C | 23°C | 23°C | 19°C | 13°C | 7°C | 2°C |
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 Point Shirley, over 2,670 vacation rentals in Orient Heights, and over 200 vacation rentals in Beachmont.
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!
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.
How much does it cost to stay in house rentals in Winthrop?
Experience the best of Winthrop with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Winthrop have air conditioning?
Absolutely! We offer over 50 house rentals with air conditioning in Winthrop. Enjoy a tailored experience with all the comforts you desire.
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.
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.
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 wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about vacation rentals in Winthrop

Total vacation rentals
Explore 190 vacation rentals in Winthrop

Nightly prices starting at
Winthrop vacation rentals start at R507 ZAR per night before taxes and fees

Verified guest reviews
Over 17,700 verified reviews to help you choose

Family-friendly vacation rentals
80 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wi-Fi availability
190 of Winthrop vacation rentals include wi-fi access

Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace across Winthrop rentals

4.8 Average rating
Winthrop stays are highly rated by guests—averaging 4.8 out of 5!

Nearby attractions
Winthrop's top spots, include Orient Heights Station, Beachmont Station, and Suffolk Downs Station
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- Hampton Beach
- Fenway Park
- TD Garden
- Harvard University
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- Brown University
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- Boston Seaport
- Boston University
- Freedom Trail
- New England Aquarium
- MIT Museum
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- Gillette Stadium
- Crane Beach
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- Roxbury Crossing Station
- Prudential Center
- Roger Williams Park Zoo




