Villa Bay - Vacation Rentals in Winthrop

Hilton Garden Inn Boston Logan Airport From US $134
         

|
9.2 (2209 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Spectacular Oceanfront 1 Bedroom Unit in Winthrop From US $354
         

10.0 (14 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Bright 2BR by Boston Waterfrontn From US $241
         

10.0 (12 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety

Luxury Places to Stay in Winthrop

Over 186+ Luxury Places to Stay in or Near Winthrop
Luxurious 1BR, Pool, Gym, nr Blue Line From US $669
         

|
New
Apartment
  • Air Conditioner
  • View
  • Security/Safety
Beautiful 4BD/2BA Gem! Near airport, city, subway! From US $627
         

6.0 (4 Reviews)
House
  • Air Conditioner
  • TV
  • Security/Safety
2 Bedroom apartment From US $597
         

|
New
Apartment
  • Air Conditioner
  • View
  • Security/Safety

Top-Rated Vacation Rentals with a Pool in Winthrop

Over 37+ Top-Rated Vacation Rentals with a Pool in or Near Winthrop
Cody's Place Winthrop Boston Logan Airport Beaches From US $335
         

10.0 (37 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Hilton Boston Logan Airport From US $187
         

|
9.0 (3617 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Comfort Inn & Suites Logan International Airport From US $110
         

9.0 (2215 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express Boston Logan Airport - Revere by IHG From US $144
         

9.0 (1298 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Staybridge Suites Boston Logan Airport - Revere by IHG From US $147
         

|
9.0 (857 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Embassy Suites Boston Logan Airport From US $147
         

|
8.8 (2162 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
TownePlace Suites Boston Logan Airport/Chelsea From US $142
         

|
8.8 (1007 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hilton Garden Inn Boston Logan Airport From US $245
         

|
8.6 (1704 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Winthrop

Over 70+ Pet-Friendly Vacation Rentals in or Near Winthrop
Cozy 3B near Beach/Boston From US $296
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy Apt, minutes from Boston! From US $375
         

9.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Jeffries Point From US $182
         

|
New
Condo
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC From US $273
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Pet-Friendly Revere Getaway, Steps from the T! From US $211
         

9.8 (60 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
50 Yards to Short Beach: Ocean-View Apt w/Deck! From US $185
         

8.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Winthrop on PetFriendly.io

Large Vacation Homes & Villas in Winthrop

Over 7+ Large Vacation Homes & Villas in or Near Winthrop
3BR1.5BA Retreat - Near Airport From US $453
         

9.8 (21 Reviews)
House
  • Child Friendly
Luxury Furnished Apartment Near Logan Airport From US $266
         

|
9.1 (20 Reviews)
Apartment
  • Air Conditioner
  • Accessibility
  • Security/Safety
Boston 4BD-5 min walk to Train&Beach/10min-Airport-Free Parking From US $375
         

9.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Furnished Apartment Near Logan Airport From US $262
         

|
8.2 (5 Reviews)
Apartment
  • Air Conditioner
  • Accessibility
  • Security/Safety
Chelsea Condo’s From US $280
         

|
6.6 (6 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Sage Apartments Boston Logan Airport Chelsea From US $420
         

|
New
Apartment
  • Air Conditioner
  • Parking
  • Accessibility
Ocean Spray Inn From US $172
         

New
House
  • Parking
  • Pet Friendly
  • Security/Safety

Wheelchair Accessible Vacation Homes in Winthrop

Over 48+ Wheelchair Accessible Vacation Homes in or Near Winthrop
Holiday Inn Express - Boston Logan Airport - Revere by IHG From US $240
         

|
8.5 (403 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Hyatt Regency Boston Harbor From US $188
         

|
9.2 (1763 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Blueground | East Boston, AC, nr parks & beach From US $157
         

Blueground | Revere, pool, nr Revere Beach From US $132
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Winthrop Varoom and Airbnb Places to Stay Under $200

Over 52+ Winthrop Varoom and Airbnb Places to Stay Under $200
Vibrant Winthrop Apartment - Close to Ocean! From US $179
         

9.8 (18 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Private Rooms, Shared Bath in a Private Home Minutes From Logan Airport From US $125
         

8.8 (638 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Guest Services
SpringHill Suites by Marriott Boston Logan Airport Revere Beach From US $155
         

Private Charming Apartment Walk to Subway & Beach From US $160
         

Blueground | Revere, washer, nr Revere Beach From US $158
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Charming B&B with AC, WiFi in Phenomenal Revere From US $143
         

New
Bed & Breakfast
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Eagles Landing - Logan Airport
New
From US $142
         

New
House
  • Air Conditioner
  • TV
  • Security/Safety

Instantly Bookable Vacation Homes in Winthrop

Over 78+ Instantly Bookable Vacation Homes in or Near Winthrop
Next to ocean, 5 min to downtown or to the airport by T From US $427
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Entire apartment, Boston in 14min, Beach in 4min! From US $220
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • TV
Modern Beachside Space - Near Boston/Airport/Train From US $202
         

9.6 (45 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Beachside condo Boston, Airport,Train From US $306
         

9.4 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Revere Vacation Rental Near MBTA ~ 7 Mi to Boston! From US $316
         

9.2 (5 Reviews)
Apartment
  • Parking
  • TV
  • Security/Safety

About Winthrop Vacation Rentals

With more than 195 Winthrop vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Villa Bay and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Winthrop.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Villa Bay Winthrop, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Winthrop. Places to stay near Winthrop are 716.25 ft² on average, with prices averaging $277 a night.

Villa Bay makes it easy and safe to find and compare vacation rentals in Winthrop with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Winthrop

Type Count
Holiday Apartments 122
Vacation Homes 27
Hotels with Suites 25
B&B 4
Villas 2

Use these Quick Filters to Find a Vacation Rental in Winthrop

Pro Tip: Villa Bay makes it easy to compare the best listings on Villa Bay homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Villa Bay homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Winthrop.

Weather in Winthrop

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