Massachusetts Winter Rental
1400 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $307/Night
For 7 Nights US $2,150
291.53 ft²
26 Guests
13 Bedrooms
13 Bathrooms
Bed & Breakfast
- Parking
- Air Conditioner
- Internet
US $168/Night
For 7 Nights US $1,176
1 Bedroom
1 Bathroom
Ocean View
Bed & Breakfast
- Spa
- Fireplace/Heating
- Ocean View
US $434/Night
For 7 Nights US $3,036
1200 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Kitchen
- Parking
US $346/Night
For 7 Nights US $2,424
12.55 ft²
15 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
Bed & Breakfast
- Skiing
- Fireplace/Heating
- Balcony/Terrace
US $170/Night
For 7 Nights US $1,190
1600 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $477/Night
For 7 Nights US $3,336
2002.09 ft²
9 Guests
4 Bedrooms
3 Bathrooms
House
- Private Beach
- Oceanfront
- Fireplace/Heating
US $259/Night
For 7 Nights US $1,813
1100 ft²
5 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cabin
- Hot Tub
- Fireplace/Heating
- Ocean View
US $307/Night
For 7 Nights US $2,150
172.22 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Bed & Breakfast
- Skiing
- Fireplace/Heating
- Balcony/Terrace
US $225/Night
For 7 Nights US $1,575
1350 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Ski Chalet
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $307/Night
For 7 Nights US $2,150
1905.21 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Parking
- Air Conditioner
- Internet
US $1,049/Night
For 7 Nights US $7,345
500 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $156/Night
For 7 Nights US $1,095
Why Choose Rent By Owner for your Massachusetts Winter Rental?
What makes our Winter Rental special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Massachusetts
How to Book Your Massachusetts Winter Rental
What's our booking process?
Our platform allows you to browse a curated selection of winter rental. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Massachusetts
Common Winter Rental Amenities
What amenities can you expect?
Our Winter Rental are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Massachusetts, MA
Barnstable County
Cape Cod
Boston
Suffolk County
Middlesex County
North Shore
Essex County
Dukes County
Martha's Vineyard
Berkshire County
The Berkshires
Yarmouth
Massachusetts Winter Rental Frequently Asked Questions
1. What are the top Winter Rentals in Massachusetts?
There are a lot of options in Massachusetts. If you plan on staying in the Massachusetts area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Winter Rentals in Massachusetts:
- Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!
- Leslie's Retreat: Spacious home ideally located to everything
- The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History
- Best of Boston Houseboat Heat/AC in Boston Harbor Suite1 in Historic Navy Yard
- Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
- Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!
- Two bedroom condo near to everything Ptown has to offer
- Lovely Dog Friendly Beach Home Close to Everything. 6 day stay open 6/28-7/4
- Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
- 4 Bedroom LUX House/with Pool Next Door
2. How many Winter Rentals are available in Massachusetts?
Currently, the total number of properties listed by RBO in 2026 is over 14114 in the Massachusetts area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Massachusetts.
More Rentals You May Like Near Massachusetts
1097.92 ft²
5 Guests
2 Bedrooms
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $268/Night
For 7 Nights US $1,874
1600 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $227/Night
For 7 Nights US $1,591
1000 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Skiing
- Fireplace/Heating
- Ocean View
US $316/Night
For 7 Nights US $2,215
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $281/Night
For 7 Nights US $1,968
850 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $320/Night
For 7 Nights US $2,238
1500 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $225/Night
For 7 Nights US $1,577
800 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $366/Night
For 7 Nights US $2,563
1100 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $357/Night
For 7 Nights US $2,501
600 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $252/Night
For 7 Nights US $1,762
1250 ft²
5 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $334/Night
For 7 Nights US $2,338
672 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $228/Night
For 7 Nights US $1,594
1700 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $286/Night
For 7 Nights US $2,002
