221+ Hotel & Resort Deals in Winthrop |
Winthrop Hotels, Resorts, and Rentals
8.7
Fabulous
(129 Reviews)
639.11 ft²
1 Bathroom
Free Cancellation
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $247/Night
For 7 Nights US $1,728
9.2
Exceptional
(1841 Reviews)
- Massachusetts
- Boston
- 1.67 mi to center
1 Bathroom
Family Friendly
Hotel
- Balcony/Terrace
- Breakfast
- Kitchen
US $315/Night
For 7 Nights US $2,205
9.2
Exceptional
(2314 Reviews)
- Boston
- Orient Heights
- 0.32 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $220/Night
For 7 Nights US $1,538
8.6
Fabulous
(1718 Reviews)
- Boston
- Harbor View - Orient Heights
- 0.32 mi to center
267.31 ft²
1 Bathroom
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $337/Night
For 7 Nights US $2,360
9.0
Exceptional
(3745 Reviews)
- Boston
- Jeffries Point
- 0.54 mi to center
1 Bathroom
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- Breakfast
US $314/Night
For 7 Nights US $2,199
8.5
Fabulous
(1705 Reviews)
- Massachusetts
- Boston
- 1.68 mi to center
340.41 ft²
8 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $271/Night
For 7 Nights US $1,900
9.0
Exceptional
(2237 Reviews)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $164/Night
For 7 Nights US $1,149
8.4
Excellent
(1397 Reviews)
332.15 ft²
7 Bathrooms
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $248/Night
For 7 Nights US $1,738
9.0
Exceptional
(1308 Reviews)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $166/Night
For 7 Nights US $1,165
5 Star Hotels in Winthrop & Winthrop Luxury Resorts
Over 17+ Luxury Hotels, Resorts, Private Villas, and 5 Star Rentals
8.2
Excellent
(2533 Reviews)
- Boston
- Jeffries Point
- 0.55 mi to center
1 Bathroom
Family Friendly
Hotel
- Private Pool
- Hot Tub
- Fireplace/Heating
US $786/Night
For 7 Nights US $5,505
8.3
Excellent
(2161 Reviews)
- Boston
- East Boston
- 0.94 mi to center
333.68 ft²
1 Bathroom
Family Friendly
Hotel
- Private Pool
- Hot Tub
- Fireplace/Heating
US $559/Night
For 7 Nights US $3,913
7.8
Very Good
(700 Reviews)
- Boston
- Harbor View - Orient Heights
- 0.50 mi to center
452.08 ft²
1 Bathroom
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $537/Night
For 7 Nights US $3,756
7.6
Very Good
(8426 Reviews)
322.92 ft²
1 Bathroom
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $455/Night
For 7 Nights US $3,188
7.4
Very Good
(239 Reviews)
279.86 ft²
12 Bathrooms
Free Cancellation
Hotel
- Private Beach
- Oceanfront
- Fireplace/Heating
US $269/Night
For 7 Nights US $1,881
7.9
Very Good
(825 Reviews)
1 Bathroom
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $261/Night
For 7 Nights US $1,825
8.8
Fabulous
(2412 Reviews)
- Boston
- East Boston
- 0.96 mi to center
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Pool
- Breakfast
US $255/Night
For 7 Nights US $1,784
8.4
Excellent
(706 Reviews)
1 Bathroom
Family Friendly
Hotel
- Balcony/Terrace
- Kitchen
- Parking
US $251/Night
For 7 Nights US $1,759
8.4
Excellent
(563 Reviews)
365.98 ft²
1 Bathroom
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $251/Night
For 7 Nights US $1,757
Best Hotels in Winthrop & Best Resorts
Over 203+ Top-Rated Hotels, Resorts, and Rentals in Winthrop
9.0
Exceptional
(913 Reviews)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $174/Night
For 7 Nights US $1,220
8.6
Fabulous
(1423 Reviews)
- Boston
- Harbor View - Orient Heights
- 0.49 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $217/Night
For 7 Nights US $1,517
8.6
Fabulous
(1232 Reviews)
1 Bathroom
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- Breakfast
US $210/Night
For 7 Nights US $1,471
8.6
Fabulous
(1001 Reviews)
1 Bathroom
Family Friendly
Hotel
- Pool
- Breakfast
- Kitchen
US $222/Night
For 7 Nights US $1,556
8.6
Fabulous
(1000 Reviews)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
US $200/Night
For 7 Nights US $1,400
8.4
Excellent
(409 Reviews)
301.39 ft²
7 Bathrooms
Free Cancellation
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $240/Night
For 7 Nights US $1,677
8.2
Excellent
(5572 Reviews)
1 Bathroom
Family Friendly
Hotel
- Pool
- Breakfast
- Kitchen
US $165/Night
For 7 Nights US $1,156
8.2
Excellent
(409 Reviews)
301.39 ft²
9 Bathrooms
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $219/Night
For 7 Nights US $1,536
New
1194.79 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Private Beach
- Oceanfront
- Pool
US $546/Night
For 7 Nights US $3,823
Cheap Hotels in Winthrop, Discounts, & Deals
Over 194+ Cheap Winthrop Hotels, Resorts, and Rentals
New
- Boston
- East Boston
- 1.05 mi to center
1 Bathroom
Family Friendly
Hotel
- Pet Friendly
- Child Friendly
US $293/Night
For 7 Nights US $2,048
8.5
Fabulous
(2 Reviews)
96.88 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- View
- Parking
US $103/Night
For 7 Nights US $718
8.8
Fabulous
(729 Reviews)
- Boston
- Eagle Hill
- 0.33 mi to center
110.33 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Air Conditioner
- Internet
- Child Friendly
US $110/Night
For 7 Nights US $772
9.0
Exceptional
(4 Reviews)
495.14 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- Parking
- Air Conditioner
US $112/Night
For 7 Nights US $782
New
399 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Pet Friendly
US $128/Night
For 7 Nights US $896
9.6
Exceptional
(41 Reviews)
750 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $130/Night
For 7 Nights US $907
New
416 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Pet Friendly
US $131/Night
For 7 Nights US $917
New
399 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Pet Friendly
US $132/Night
For 7 Nights US $924
New
519 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Pet Friendly
US $133/Night
For 7 Nights US $931
Hotels Near Winthrop & Other Nearby Resorts
Over 185+ Hotels in Winthrop and Other Resorts & Rentals Nearby
10.0
Exceptional
(8 Reviews)
- Boston
- Harbor View - Orient Heights
- 0.09 mi to center
904.17 ft²
6 Guests
3 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- Spa
- Fireplace/Heating
- View
US $466/Night
For 7 Nights US $3,264
8.8
Fabulous
(212 Reviews)
1 Bedroom
1 Bathroom
Couples Retreat
Bed & Breakfast
- Breakfast
- Parking
- Air Conditioner
US $211/Night
For 7 Nights US $1,478
10.0
Exceptional
(3 Reviews)
1194.79 ft²
8 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- View
- Air Conditioner
US $330/Night
For 7 Nights US $2,310
10.0
Exceptional
(52 Reviews)
1200 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
US $313/Night
For 7 Nights US $2,189
10.0
Exceptional
(2 Reviews)
- Boston
- Central-Maverick Square - Paris Street
- 0.29 mi to center
904.17 ft²
6 Guests
2 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- View
- Air Conditioner
- Internet
US $374/Night
For 7 Nights US $2,617
New
- Boston
- East Boston
- 0.80 mi to center
750 ft²
6 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $420/Night
For 7 Nights US $2,937
10.0
Exceptional
(2 Reviews)
- Boston
- East Boston
- 0.80 mi to center
75.35 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
US $316/Night
For 7 Nights US $2,211
New
- Boston
- Jeffries Point
- 1.12 mi to center
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $182/Night
For 7 Nights US $1,277
9.7
Exceptional
(3 Reviews)
2604.87 ft²
10 Guests
4 Bedrooms
4 Bathrooms
Villa
- Fireplace/Heating
- Balcony/Terrace
- View
US $1,247/Night
For 7 Nights US $8,729
Winthrop Vacation Rentals, Villas, & Hotel Suites
Over 158+ Winthrop Vacation Rentals, Cabins, Cottages, Condos & Holiday Homes
9.3
Exceptional
(9 Reviews)
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pet Friendly
- Air Conditioner
- Internet
US $375/Night
For 7 Nights US $2,625
New
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Child Friendly
US $240/Night
For 7 Nights US $1,680
9.1
Exceptional
(20 Reviews)
764.24 ft²
12 Guests
6 Bedrooms
6 Bathrooms
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
US $266/Night
For 7 Nights US $1,865
9.0
Exceptional
(6 Reviews)
947.22 ft²
6 Guests
3 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- Fireplace/Heating
- Parking
- Internet
US $660/Night
For 7 Nights US $4,622
8.0
Excellent
(2 Reviews)
1496.18 ft²
8 Guests
3 Bedrooms
1 Bathroom
Apartment
- Fireplace/Heating
- Parking
- Air Conditioner
US $329/Night
For 7 Nights US $2,306
7.9
Very Good
(183 Reviews)
226.04 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Parking
- Air Conditioner
US $186/Night
For 7 Nights US $1,300
6.5
Good
(2 Reviews)
904.17 ft²
3 Guests
2 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- Fireplace/Heating
- Parking
- Internet
US $298/Night
For 7 Nights US $2,088
New
- Boston
- Central-Maverick Square - Paris Street
- 0.21 mi to center
1399.31 ft²
6 Guests
3 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- Fireplace/Heating
- View
- Air Conditioner
US $1,806/Night
For 7 Nights US $12,639
New
- Boston
- Central-Maverick Square - Paris Street
- 0.21 mi to center
1194.79 ft²
6 Guests
3 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- Fireplace/Heating
- View
- Air Conditioner
US $1,351/Night
For 7 Nights US $9,454
Pet Friendly Hotels in Winthrop
Over 59+ Hotels, Inns, Motels, Resorts, & Rentals that Accept Pets
New
1097.92 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Free Cancellation
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $878/Night
For 7 Nights US $6,144
New
1302.43 ft²
6 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Fireplace/Heating
- Balcony/Terrace
- View
US $400/Night
For 7 Nights US $2,802
New
- Boston
- Harbor View - Orient Heights
- 0.08 mi to center
968.75 ft²
16 Guests
7 Bedrooms
6 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $262/Night
For 7 Nights US $1,835
New
- Boston
- East Boston
- 0.96 mi to center
6 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pet Friendly
- Parking
- Air Conditioner
US $899/Night
For 7 Nights US $6,294
New
- Boston
- Harbor View - Orient Heights
- 0.15 mi to center
1001.04 ft²
6 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Pet Friendly
- Parking
- Air Conditioner
US $350/Night
For 7 Nights US $2,450
New
184.06 ft²
32 Guests
10 Bedrooms
10 Bathrooms
Ocean View
House
- Private Beach
- Oceanfront
- Fireplace/Heating
US $172/Night
For 7 Nights US $1,205
Last Minute Hotel Deals, Rentals, & Hotels Tonight
Over 84+ Book a Last Minute Hotel in Winthrop and Save 30-50%
New
- Boston
- Harbor View - Orient Heights
- 0.07 mi to center
904.17 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
Apartment
- Fireplace/Heating
- Parking
- Air Conditioner
US $258/Night
For 7 Nights US $1,808
New
2 Guests
1 Bedroom
1 Bathroom
Apartment
- View
- Parking
- Air Conditioner
US $134/Night
For 7 Nights US $938
Book a Last Minute Place to Stay in Winthrop
About Winthrop Vacation Rentals
There are more than 221 places to stay in Winthrop that are available. These options include hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many places to stay in Winthrop.
Are you seeking a last-minute hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With Hotala Winthrop, you can quickly compare different options to find the hottest deals with a single click. Looking for a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Winthrop. Places to stay near Winthrop are 682.75 ft² on average, with prices averaging US $339 a night.
Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Winthrop with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your reservation today.
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Top Hotels, Resorts, Rentals, Villas, Vacation Homes, Cottages, B&B and Cabins Accommodation Types in Winthrop
| Type | Count |
|---|---|
| Holiday Apartments | 139 |
| Vacation Homes | 29 |
| B&B | 5 |
| Villas | 2 |
Use these Quick Filters to Find a Vacation Rental in Winthrop
★ Pro Tip: Hotala has aggregated the supply of many of the leading websites including providers of short-term rentals, OTAs (including Booking.com, Agoda, Airbnb, and others). Use the Advanced Filter feature at the top to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and more. We want to help you find the hottest places and best places to stay in Winthrop.
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
Stay Near Winthrop's Top Attractions
Hotala can help you find hotels, resorts, and rentals near many of Winthrop's top attractions, neighborhoods, and points of interest.
Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods
Frequently Asked Questions About Winthrop?
What are the top hotels or resorts in Winthrop?
You have a lot of choices in or near Winthrop. If you need a hotel in the Winthrop area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in Winthrop:
- Hilton Garden Inn Boston Logan Airport
- Hyatt Regency Boston Harbor
- Hilton Boston Logan Airport
- Comfort Inn & Suites Logan International Airport
- Holiday Inn Express Boston Logan Airport - Revere by IHG
- Staybridge Suites Boston Logan Airport - Revere by IHG
- Embassy Suites Boston Logan Airport
- Staybridge Suites - Boston Logan Airport - Revere by IHG
- Hilton Garden Inn Boston Logan Airport
- Courtyard by Marriott Boston Logan Airport
How many hotels, resorts, or rentals are available in Winthrop?
At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2026 is over 221 in the Winthrop area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Winthrop.
Nearby Neighborhood (2)
| Neighborhood | Property Count |
|---|---|
| East Boston Hotel & Resort Deals in Boston, Massachusetts | 71 |
| Harbor View - Orient Heights Hotel & Resort Deals in Boston, Massachusetts | 699 |
People Also Ask
Finding the best prices in Winthrop
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