Apartment
10.0(58 Reviews)
2 Bedrooms
6 Guests
Parking
Ocean View
Balcony/Terrace
View
US $403/Night
7 Nights - US $2,823
Winthrop Holiday Rentals
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Compare Villas, Resorts, & Rentals in Winthrop
10.0
Apartment
10.0(10 Reviews)
3 Bedrooms
6 Guests
- Parking
- View
Internet
Child Friendly
US $466/Night
7 Nights - US $3,264
Bed & Breakfast
8.6(228 Reviews)
1 Bedroom
Breakfast- Parking
Air Conditioner- Internet
US $211/Night
7 Nights - US $1,478
Apartment
10.0(50 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $253/Night
7 Nights - US $1,772
Apartment
10.0(3 Reviews)
3 Bedrooms
8 Guests
- View
- Air Conditioner
- Internet
Laundry
US $330/Night
7 Nights - US $2,310
Apartment
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
Kitchen- Air Conditioner
US $342/Night
7 Nights - US $2,396
Apartment
10.0(3 Reviews)
2 Bedrooms
4 Guests
Oceanfront- Parking
- Ocean View
- View
US $246/Night
7 Nights - US $1,722
Apartment
10.0(2 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $489/Night
7 Nights - US $3,420
House
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $425/Night
7 Nights - US $2,976
Luxury Holiday Rentals in Winthrop
Over 251+ Luxury Holiday Rentals in or Near Winthrop
House
9.0(6 Reviews)
6 Bedrooms
16 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $1,784/Night
7 Nights - US $12,488
House
10.0(2 Reviews)
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,201/Night
7 Nights - US $8,408
House
6 Bedrooms
16 Guests
- Breakfast
- Parking
- Balcony/Terrace
- View
US $1,199/Night
7 Nights - US $8,393
Villa
9.8(4 Reviews)
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $1,188/Night
7 Nights - US $8,319
House
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $878/Night
7 Nights - US $6,144
Villa
9.8(143 Reviews)
4 Bedrooms
8 Guests
- Oceanfront
Hot Tub- Parking
- Ocean View
US $798/Night
7 Nights - US $5,584
House
4 Bedrooms
8 Guests
- Hot Tub
- Ocean View
- Balcony/Terrace
- View
US $688/Night
7 Nights - US $4,815
Hotel
9.2(1453 Reviews)
- Breakfast
- Parking
Pool- Balcony/Terrace
US $658/Night
7 Nights - US $4,605
Apartment
9.6(5 Reviews)
3 Bedrooms
10 Guests
- Kitchen
- Air Conditioner
- Internet
Pet Friendly
US $590/Night
7 Nights - US $4,128
Top-Rated Holiday Rentals with a Pool in Winthrop
Over 38+ The Best Private Villas and Holiday Rentals in Winthrop with a Pool
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $130/Night
7 Nights - US $908
Apartment
9.8(47 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $337/Night
7 Nights - US $2,361
Hotel
9.2(2291 Reviews)
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $429/Night
7 Nights - US $3,000
US $335/Night
7 Nights - US $2,342
Hotel
9.0(1001 Reviews)
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $232/Night
7 Nights - US $1,626
US $374/Night
7 Nights - US $2,617
Hotel
8.6(1740 Reviews)
Private Pool
EV Charge Station- Parking
- Pool
US $375/Night
7 Nights - US $2,628
Hotel
8.6(1309 Reviews)
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $217/Night
7 Nights - US $1,517
Hotel
8.6(1296 Reviews)
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $186/Night
7 Nights - US $1,302
Pet-Friendly Holiday Rentals in Winthrop
Over 86+ Pet-Friendly Holiday Rentals in or Near Winthrop
Condo
10.0(1 Review)
2 Bedrooms
4 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $398/Night
7 Nights - US $2,785
Apartment
10.0(2 Reviews)
1 Bedroom
6 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $516/Night
7 Nights - US $3,613
US $182/Night
7 Nights - US $1,277
House
9.8(65 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $324/Night
7 Nights - US $2,268
Apartment
10.0(1 Review)
1 Bedroom
4 Guests
- Hot Tub
- Balcony/Terrace
- View
- Air Conditioner
US $238/Night
7 Nights - US $1,668
Apartment
9.8(29 Reviews)
1 Bedroom
3 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $346/Night
7 Nights - US $2,423
Apartment
9.6(5 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $399/Night
7 Nights - US $2,795
Condo
8.8(6 Reviews)
2 Bedrooms
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $430/Night
7 Nights - US $3,013
Apartment
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $479/Night
7 Nights - US $3,355
Large Holiday Rentals and Private Villas in Winthrop
Over 10+ Large Holiday Rentals and Private Villas in or Near Winthrop
Apartment
8.0(1 Review)
2 Bedrooms
31 Guests
- Air Conditioner
- Internet
- Child Friendly
Bedding/Linens
US $215/Night
7 Nights - US $1,507
Apartment
8.3(48 Reviews)
6 Bedrooms
12 Guests
- Air Conditioner
- Internet
- Child Friendly
Accessibility
US $266/Night
7 Nights - US $1,865
Apartment
9.8(6 Reviews)
4 Bedrooms
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $408/Night
7 Nights - US $2,856
House
8.2(97 Reviews)
12 Bedrooms
40 Guests
Private Beach- Oceanfront
- Parking
- Ocean View
US $172/Night
7 Nights - US $1,205
House
6.4(5 Reviews)
4 Bedrooms
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $282/Night
7 Nights - US $1,977
Apartment
7.3(33 Reviews)
7 Bedrooms
16 Guests
- View
- Air Conditioner
- Internet
- Child Friendly
US $262/Night
7 Nights - US $1,835
Apartment
3 Bedrooms
10 Guests
- Child Friendly
US $498/Night
7 Nights - US $3,487
House
9.8(22 Reviews)
3 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $540/Night
7 Nights - US $3,781
Apartment
3 Bedrooms
12 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $421/Night
7 Nights - US $2,947
Wheelchair Accessible Holiday Homes in Winthrop
Over 54+ Wheelchair Accessible Holiday Homes in or Near Winthrop
Apartment
1 Bedroom
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $362/Night
7 Nights - US $2,537
Hotel
8.5(1705 Reviews)
- Breakfast
- Parking
- Balcony/Terrace
- Air Conditioner
US $182/Night
7 Nights - US $1,273
Hotel
8.6(1012 Reviews)
- Breakfast
- Parking
- Pool
- Kitchen
US $155/Night
7 Nights - US $1,087
Apartment
1 Bedroom
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $347/Night
7 Nights - US $2,428
Hotel
8.5(396 Reviews)
- Private Pool
- Breakfast
- EV Charge Station
- Parking
US $112/Night
7 Nights - US $786
Apartment
1 Bedroom
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $321/Night
7 Nights - US $2,245
Apartment
1 Bedroom
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $282/Night
7 Nights - US $1,971
Apartment
1 Bedroom
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $280/Night
7 Nights - US $1,962
Apartment
1 Bedroom
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $192/Night
7 Nights - US $1,344
Winthrop Private Villas and Holiday Homes Under $200
Over 75+ Winthrop Private Villas and Holiday Homes Under $200
House
10.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $190/Night
7 Nights - US $1,332
House
9.3(8 Reviews)
1 Bedroom
2 Guests
- Parking
- Air Conditioner
- Internet
- Laundry
US $112/Night
7 Nights - US $782
Hotel
8.6(1005 Reviews)
- Breakfast
- Parking
- Pool
- Kitchen
US $166/Night
7 Nights - US $1,165
Apartment
9.6(70 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $118/Night
7 Nights - US $825
House
8.9(749 Reviews)
4 Bedrooms
8 Guests
- Air Conditioner
- Internet
- Child Friendly
Security/Safety
US $110/Night
7 Nights - US $772
Apartment
1 Bedroom
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $181/Night
7 Nights - US $1,269
Apartment
2 Bedrooms
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $155/Night
7 Nights - US $1,085
Bed & Breakfast
1 Bedroom
6 Guests
- Air Conditioner
- Internet
- Child Friendly
- Bedding/Linens
US $155/Night
7 Nights - US $1,085
US $151/Night
7 Nights - US $1,056
Instantly Bookable Holiday Homes in Winthrop
Over 124+ Instantly Bookable Holiday Homes in or Near Winthrop
Apartment
9.8(44 Reviews)
2 Bedrooms
5 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $306/Night
7 Nights - US $2,144
Apartment
10.0(52 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $313/Night
7 Nights - US $2,189
Apartment
9.6(8 Reviews)
2 Bedrooms
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $341/Night
7 Nights - US $2,384
Apartment
9.4(54 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $300/Night
7 Nights - US $2,099
Apartment
9.4(8 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $385/Night
7 Nights - US $2,696
Apartment
9.4(8 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $288/Night
7 Nights - US $2,013
Apartment
9.0(17 Reviews)
1 Bedroom
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $270/Night
7 Nights - US $1,892
Apartment
7.6(5 Reviews)
2 Bedrooms
3 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $352/Night
7 Nights - US $2,463
Apartment
6.0(1 Review)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $447/Night
7 Nights - US $3,128
Book a Last Minute Place to Stay in Winthrop
About Casai's Private Villas and Holiday Rentals in Winthrop
Discover more than 260 vacation rentals available in Winthrop. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Winthrop.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winthrop, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Winthrop. On average, places to stay near Winthrop offer 560.72 ft², with nightly prices averaging US $305.
With Casai, finding and comparing holiday rentals in Winthrop is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other places to stay near the Winthrop, MA
There are 260 Winthrop, MA Holiday Rentals
- Prices for a holiday home in Winthrop start at US $79
- Top rated vacation home in Winthrop is Casa de Los Clarey Boston Logan Beaches Free Parking
- Most popular short term in Winthrop is Hampton Inn Boston Logan Airport
- Cheapest place to stay in Winthrop is Blueground | East Boston, AC, nr parks & beach
- Most expensive holiday rental in Winthrop is Luxury Victorian near Salem: Stunning Ocean Views & Modern Elegance in 6BR Manor
Recently Booked Holiday Rentals in Winthrop
Frequently Asked Questions About Winthrop?
What are the top holiday rentals in Winthrop?
With numerous options available in Winthrop, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Winthrop:
- 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
- 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
- Luxury 3BD Short Walk to Airport
How many holiday rentals have private pools in Winthrop?
Discover a selection of holiday rentals with private pools near Winthrop with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Winthrop are best for families?
If you're searching for a family-friendly holiday home in Winthrop, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Winthrop:
How many Casai.com holiday rentals are available in Winthrop?
As of 2026, Casai boasts over 260 properties listed in the Winthrop area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winthrop.
Nearby Neighborhood (2)
| Neighborhood | Property Count |
|---|---|
| East Boston Vacation Rentals in Boston, Massachusetts | 74 |
| Harbor View - Orient Heights Vacation Rentals in Boston, Massachusetts | 774 |
