Winthrop Vacation Rentals & Ski-in/Ski-out Homes
Apartment
10.0Exceptional
(57 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
Oceanfront
Parking
Ocean View
Balcony/Terrace
US $355/Night
7 Nights - US $2,487
Apartment
- Boston
- ·
- Harbor View - Orient Heights
- 0.09 mi to center
10.0Exceptional
(10 Reviews)
3 Bedrooms
1 Bath
6 Guests
904.17 ft²
- Parking
View
Internet
Child Friendly
US $466/Night
7 Nights - US $3,264
Bed & Breakfast
8.8Fabulous
(226 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
Air Conditioner- Internet
US $218/Night
7 Nights - US $1,525
Apartment
10.0Exceptional
(48 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $253/Night
7 Nights - US $1,768
Apartment
10.0Exceptional
(3 Reviews)
3 Bedrooms
1 Bath
8 Guests
1194.79 ft²
- View
- Air Conditioner
- Internet
Laundry
US $330/Night
7 Nights - US $2,310
Apartment
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
Kitchen- Air Conditioner
US $342/Night
7 Nights - US $2,396
Apartment
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
950 ft²
- Oceanfront
- Parking
- Ocean View
- View
US $246/Night
7 Nights - US $1,722
Apartment
- Boston
- ·
- Harbor View - Orient Heights
- 0.40 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
1000 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $489/Night
7 Nights - US $3,420
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
2176 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $420/Night
7 Nights - US $2,937
Luxury Places to Stay in Winthrop
Over 245+ Luxury Places to Stay in or Near Winthrop
House
9.0Exceptional
(6 Reviews)
6 Bedrooms
3 Baths
16 Guests
4500 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $1,823/Night
7 Nights - US $12,761
House
- Boston
- ·
- East Boston
- 0.57 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
4 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,201/Night
7 Nights - US $8,408
House
6 Bedrooms
5 Baths
16 Guests
4499.31 ft²
- Breakfast
- Parking
- Balcony/Terrace
- View
US $1,199/Night
7 Nights - US $8,393
Villa
- Boston
- ·
- Harbor View - Orient Heights
- 0.58 mi to center
9.8Exceptional
(4 Reviews)
4 Bedrooms
4 Baths
10 Guests
2604.87 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $1,188/Night
7 Nights - US $8,319
New
House
- Boston
- ·
- Eagle Hill
- 0.14 mi to center
4 Bedrooms
2 Baths
8 Guests
- Oceanfront
Hot Tub- Ocean View
- Balcony/Terrace
US $883/Night
7 Nights - US $6,182
House
2 Bedrooms
2 Baths
4 Guests
1097.92 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $878/Night
7 Nights - US $6,144
House
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
8 Guests
4000 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $582/Night
7 Nights - US $4,071
Apartment
- Boston
- ·
- Harbor View - Orient Heights
- 0.62 mi to center
10.0Exceptional
(4 Reviews)
3 Bedrooms
1 Bath
10 Guests
- Air Conditioner
- Internet
Pet Friendly- Child Friendly
US $547/Night
7 Nights - US $3,830
Apartment
2 Bedrooms
2 Baths
6 Guests
1194.79 ft²
Private Beach- Oceanfront
- Parking
Pool
US $546/Night
7 Nights - US $3,823
Top-Rated Vacation Rentals with a Pool in Winthrop
Over 37+ Top-Rated Vacation Rentals with a Pool in or Near Winthrop
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
683 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $139/Night
7 Nights - US $973
Hotel
- Boston
- ·
- Orient Heights
- 0.32 mi to center
9.2Exceptional
(2282 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $288/Night
7 Nights - US $2,015
Hotel
9.2Exceptional
(1433 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $390/Night
7 Nights - US $2,729
Hotel
- Boston
- ·
- Jeffries Point
- 0.54 mi to center
9.0Exceptional
(3926 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $402/Night
7 Nights - US $2,817
Hotel
9.0Exceptional
(1000 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $289/Night
7 Nights - US $2,025
Hotel
- Boston
- ·
- East Boston
- 0.96 mi to center
8.8Fabulous
(2639 Reviews)
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
US $345/Night
7 Nights - US $2,418
Hotel
- Boston
- ·
- Harbor View - Orient Heights
- 0.32 mi to center
8.6Fabulous
(1740 Reviews)
1 Bath
267.31 ft²
Private Pool
EV Charge Station- Parking
- Pool
US $375/Night
7 Nights - US $2,628
Hotel
- Boston
- ·
- Harbor View - Orient Heights
- 0.49 mi to center
8.6Fabulous
(1301 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $276/Night
7 Nights - US $1,933
Hotel
8.6Fabulous
(1296 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $324/Night
7 Nights - US $2,266
Pet-Friendly Vacation Rentals in Winthrop
Over 86+ Pet-Friendly Vacation Rentals in or Near Winthrop
Condo
- Boston
- ·
- East Boston
- 1.12 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
700 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $397/Night
7 Nights - US $2,780
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
6 Guests
1302.43 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $516/Night
7 Nights - US $3,613
Condo
- Boston
- ·
- Jeffries Point
- 1.12 mi to center
1 Bedroom
1 Bath
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Pet Friendly
US $182/Night
7 Nights - US $1,277
House
9.8Exceptional
(65 Reviews)
2 Bedrooms
1 Bath
4 Guests
1100 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $324/Night
7 Nights - US $2,268
New
Apartment
- Boston
- ·
- Eagle Hill
- 0.14 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
548.96 ft²
- Hot Tub
- Balcony/Terrace
- View
- Air Conditioner
US $238/Night
7 Nights - US $1,668
Apartment
9.8Exceptional
(29 Reviews)
1 Bedroom
1 Bath
3 Guests
700 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $346/Night
7 Nights - US $2,423
Apartment
9.6Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
2000 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $399/Night
7 Nights - US $2,795
Condo
8.8Fabulous
(6 Reviews)
2 Bedrooms
1 Bath
6 Guests
1400 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $430/Night
7 Nights - US $3,013
Apartment
- Boston
- ·
- Harbor View - Orient Heights
- 0.42 mi to center
2 Bedrooms
2 Baths
4 Guests
1110 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $525/Night
7 Nights - US $3,678
Large Vacation Homes & Villas in Winthrop
Over 11+ Large Vacation Homes & Villas in or Near Winthrop
Apartment
8.0Excellent
(1 Review)
2 Bedrooms
1 Bath
31 Guests
800 ft²
- Air Conditioner
- Internet
- Child Friendly
Bedding/Linens
US $215/Night
7 Nights - US $1,507
House
8.4Excellent
(60 Reviews)
12 Bedrooms
13 Baths
39 Guests
195.54 ft²
- Private Beach
- Oceanfront
- Parking
- Ocean View
US $172/Night
7 Nights - US $1,205
Apartment
9.6Exceptional
(5 Reviews)
4 Bedrooms
1 Bath
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Laundry
US $401/Night
7 Nights - US $2,809
Apartment
- Boston
- ·
- East Boston
- 0.95 mi to center
8.3Excellent
(46 Reviews)
6 Bedrooms
6 Baths
12 Guests
764.24 ft²
- Air Conditioner
- Internet
- Child Friendly
Accessibility
US $266/Night
7 Nights - US $1,865
House
- Boston
- ·
- East Boston
- 0.93 mi to center
6.4Good
(5 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $529/Night
7 Nights - US $3,702
Apartment
- Boston
- ·
- Harbor View - Orient Heights
- 0.08 mi to center
7.2Very Good
(31 Reviews)
7 Bedrooms
6 Baths
16 Guests
968.75 ft²
- View
- Air Conditioner
- Internet
- Child Friendly
US $262/Night
7 Nights - US $1,835
Apartment
3 Bedrooms
1 Bath
10 Guests
- Child Friendly
US $498/Night
7 Nights - US $3,487
House
9.8Exceptional
(22 Reviews)
3 Bedrooms
1 Bath
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $540/Night
7 Nights - US $3,781
Apartment
- Boston
- ·
- Eagle Hill
- 0.09 mi to center
3 Bedrooms
1 Bath
12 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $421/Night
7 Nights - US $2,947
Wheelchair Accessible Vacation Homes in Winthrop
Over 54+ Wheelchair Accessible Vacation Homes in or Near Winthrop
Apartment
1 Bedroom
1 Bath
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $363/Night
7 Nights - US $2,544
Hotel
- Massachusetts
- ·
- Boston
- 1.68 mi to center
8.5Fabulous
(1705 Reviews)
8 Baths
340.41 ft²
- Breakfast
- Parking
- Balcony/Terrace
- Air Conditioner
US $182/Night
7 Nights - US $1,273
Hotel
8.6Fabulous
(1024 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $279/Night
7 Nights - US $1,955
New
Apartment
1 Bedroom
1 Bath
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $347/Night
7 Nights - US $2,428
Hotel
8.5Fabulous
(396 Reviews)
7 Baths
301.39 ft²
- Private Pool
- Breakfast
- EV Charge Station
- Parking
US $112/Night
7 Nights - US $786
New
Apartment
1 Bedroom
1 Bath
6 Guests
1001 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $321/Night
7 Nights - US $2,245
Apartment
1 Bedroom
1 Bath
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $282/Night
7 Nights - US $1,971
New
Apartment
1 Bedroom
1 Bath
6 Guests
1001 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $280/Night
7 Nights - US $1,962
New
Apartment
1 Bedroom
1 Bath
6 Guests
1001 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $192/Night
7 Nights - US $1,344
Winthrop Resorts and Airbnb Homes Under $200
Over 75+ Winthrop Resorts and Airbnb Homes Under $200
House
- Boston
- ·
- Eagle Hill
- 0.12 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $190/Night
7 Nights - US $1,332
Apartment
9.5Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- View
- Air Conditioner
- Internet
US $134/Night
7 Nights - US $938
Apartment
9.6Exceptional
(70 Reviews)
1 Bedroom
1 Bath
3 Guests
750 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $118/Night
7 Nights - US $825
House
- Boston
- ·
- Eagle Hill
- 0.34 mi to center
9.3Exceptional
(8 Reviews)
1 Bedroom
1 Bath
2 Guests
495.14 ft²
- Parking
- Air Conditioner
- Internet
- Laundry
US $112/Night
7 Nights - US $782
Apartment
- Boston
- ·
- Central-Maverick Square - Paris Street
- 0.29 mi to center
9.6Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
6 Guests
900 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $159/Night
7 Nights - US $1,113
Apartment
1 Bedroom
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $181/Night
7 Nights - US $1,269
Apartment
2 Bedrooms
2 Baths
4 Guests
977 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $165/Night
7 Nights - US $1,156
Bed & Breakfast
1 Bedroom
1 Bath
6 Guests
- Air Conditioner
- Internet
- Child Friendly
- Bedding/Linens
US $157/Night
7 Nights - US $1,100
Apartment
- Boston
- ·
- Jeffries Point
- 0.73 mi to center
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $151/Night
7 Nights - US $1,056
Instantly Bookable Vacation Homes in Winthrop
Over 122+ Instantly Bookable Vacation Homes in or Near Winthrop
Apartment
- Boston
- ·
- Jeffries Point
- 1.14 mi to center
9.8Exceptional
(44 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $306/Night
7 Nights - US $2,144
Apartment
10.0Exceptional
(52 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $313/Night
7 Nights - US $2,189
Apartment
9.6Exceptional
(51 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $282/Night
7 Nights - US $1,974
Apartment
- Boston
- ·
- Eagle Hill
- 0.06 mi to center
9.4Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $385/Night
7 Nights - US $2,696
Apartment
9.4Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $288/Night
7 Nights - US $2,013
Apartment
9.0Exceptional
(17 Reviews)
1 Bedroom
1 Bath
4 Guests
600 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $270/Night
7 Nights - US $1,892
Apartment
7.6Very Good
(5 Reviews)
2 Bedrooms
1 Bath
3 Guests
900 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $347/Night
7 Nights - US $2,429
Apartment
6.0Good
(1 Review)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $311/Night
7 Nights - US $2,178
Apartment
- Boston
- ·
- Jeffries Point
- 0.99 mi to center
2 Bedrooms
1 Bath
5 Guests
750 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $421/Night
7 Nights - US $2,946
Book a Last Minute Place to Stay in Winthrop
About Winthrop Vacation Rentals
Explore over 254 vacation rentals in Winthrop with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Winthrop for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Winthrop. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Winthrop tailored to your preferences. On average, these rentals offer 552.36 ft² of space, and are priced at an average of US $304 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Winthrop at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
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Top Types of Ski Accommodations in Winthrop
| Type | Count |
|---|---|
| Holiday Apartments | 165 |
| Vacation Homes | 41 |
| B&B | 5 |
| Villas | 1 |
Use these Quick Filters to Find a Vacation Rental in Winthrop
★ Pro Tip: Discover Your Ideal Vacation Rental in Winthrop with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
Weather in Winthrop, MA
View the weather forecast for Winthrop before booking your Winthrop Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Winthrop, MA
Sunski offers a large selection of top attractions around Winthrop . Research things to do on your vacation before you visit Winthrop.
Other Places to Stay in Winthrop, MA
Frequently Asked Questions About Winthrop?
What are the top vacation rentals in Winthrop?
When organizing your trip to Winthrop, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Winthrop. Peruse our collection of highly-rated properties and secure your reservation today.
- Casa de Los Clarey Boston Logan Beaches Free Parking
- Stunning 1 BR-Apt-Oceanview to Revere Beach -3 Train Stop Boston Logan Airport
- The Princeton Boston - Luxurious Apartment - New - Near Downtown Boston, Airport
- Walk to Constitution Beach: Mid-Century Boston Gem
- Walk to Constitution Beach: Mid-Century Boston Gem
- Family-Friendly 3BR Easy Blue Line Access Near Boston
- North Shore Luxury Suite
- Stylish 3BR Revere Home Sleeps 8 Near Boston, Revere Beach and Airport
- Entire apartment, Boston in 14min, Beach in 4min!
- Waterfront Escape - Spectacular Views, Only 5 Minutes from Boston Airport
How many vacation rentals have private pools in Winthrop?
Uncover 9 vacation rentals boasting private pools near Winthrop. Explore top-rated RBO homes offering access to a swimming pool:
- Holiday Inn Boston Logan Airport - Chelsea by IHG
- Embassy Suites Boston at Logan Airport
- Comfort Inn & Suites Logan International Airport
- Staybridge Suites - Boston Logan Airport - Revere by IHG
Which vacation homes or resorts in Winthrop are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Winthrop. Enjoy great views, locations and save money with SunSki Resorts.™
- Luxury, New 2-Bedroom Condo Near Airport/Boston/Train
- Cozy Apt, minutes from Boston!
- Holiday Inn Boston Logan Airport - Chelsea by IHG
How many SunSkiResorts vacation rentals or resorts are available in Winthrop?
Discover the ideal vacation rental in Winthrop with SunSki Resorts™. We provide an extensive selection of over 254 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Winthrop.
Nearby Neighborhood (2)
| Neighborhood | Property Count |
|---|---|
| East Boston Vacation Rentals in Boston, Massachusetts | 72 |
| Harbor View - Orient Heights Vacation Rentals in Boston, Massachusetts | 775 |
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