Estia Villas - Vacation Rentals in Windsor
House
10.0
(
26 Reviews
)
4 Bedrooms
1 Bathroom
10 Guests
-
Parking -
Ocean View -
Balcony/Terrace -
View
US $350
/Night
7 Nights - $2,449
House
10.0
(
2 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
2034.38 ft²
-
Parking
-
View
-
Internet -
Sports/Activities
US $531
/Night
7 Nights - $3,718
Cabin
10.0
(
13 Reviews
)
1 Bedroom
2 Bathrooms
12 Guests
1425 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen -
Air Conditioner
US $349
/Night
7 Nights - $2,446
Cabin
10.0
(
7 Reviews
)
2 Bedrooms
1 Bathroom
7 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $355
/Night
7 Nights - $2,487
House
10.0
(
4 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
1500 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $674
/Night
7 Nights - $4,717
Cabin
10.0
(
3 Reviews
)
5 Bedrooms
1 Bathroom
12 Guests
1496 ft²
-
Oceanfront -
Parking
-
Ocean View
-
Balcony/Terrace
US $844
/Night
7 Nights - $5,907
Cabin
10.0
(
3 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
2034 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $431
/Night
7 Nights - $3,015
House
10.0
(
1 Review
)
9 Bedrooms
4 Bathrooms
20 Guests
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $1,121
/Night
7 Nights - $7,849
See More Windsor Vacation Rentals
Luxury Places to Stay in Windsor
Over 56+
Luxury Places to Stay in or Near Windsor
House
1 Bedroom
1 Bathroom
11 Guests
-
Internet
-
Laundry -
Bedding/Linens -
Wellness Facilities
US $985
/Night
7 Nights - $6,896
House
5 Bedrooms
2 Bathrooms
16 Guests
1496.18 ft²
-
Oceanfront
-
Parking
-
Skiing -
Ocean View
US $583
/Night
7 Nights - $4,081
House
9.8
(
10 Reviews
)
4 Bedrooms
2 Bathrooms
12 Guests
-
Hot Tub -
Parking
-
Pool -
Ocean View
US $545
/Night
7 Nights - $3,813
New
Cabin
4 Bedrooms
2 Bathrooms
8 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $538
/Night
7 Nights - $3,767
House
9.2
(
18 Reviews
)
5 Bedrooms
2 Bathrooms
12 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
View
US $497
/Night
7 Nights - $3,477
House
8.4
(
25 Reviews
)
5 Bedrooms
3 Bathrooms
16 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $454
/Night
7 Nights - $3,177
House
2 Bedrooms
1 Bathroom
6 Guests
947.22 ft²
-
Parking
-
Skiing
-
View
-
Air Conditioner
US $447
/Night
7 Nights - $3,130
New
House
4 Bedrooms
2 Bathrooms
7 Guests
-
Internet
-
Laundry
-
Bedding/Linens
-
Wellness Facilities
US $420
/Night
7 Nights - $2,943
See More Windsor Luxury Vacation Rentals
Find More Windsor Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Windsor
Over 2+
Top-Rated Vacation Rentals with a Pool in or Near Windsor
House
9.6
(
10 Reviews
)
2 Bedrooms
1 Bathroom
8 Guests
1100 ft²
-
Hot Tub
-
Parking
-
Pool
-
Ocean View
US $289
/Night
7 Nights - $2,021
House
9.4
(
16 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
1500 ft²
-
Private Pool -
Hot Tub
-
Parking
-
Pool
US $296
/Night
7 Nights - $2,070
See More Windsor Vacation Rentals with a Pool
Pet-Friendly Vacation Rentals in Windsor
Over 16+
Pet-Friendly Vacation Rentals in or Near Windsor
New
Cabin
8.0
(
4 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Balcony/Terrace
-
Internet
-
Pet Friendly -
Child Friendly
US $302
/Night
7 Nights - $2,111
House
2 Bedrooms
2 Bathrooms
9 Guests
2002.09 ft²
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Pet Friendly
US $367
/Night
7 Nights - $2,567
House
9.8
(
73 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
1320 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $324
/Night
7 Nights - $2,271
Cottage
9.8
(
51 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
864 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $310
/Night
7 Nights - $2,168
House
9.2
(
30 Reviews
)
4 Bedrooms
2 Bathrooms
10 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $410
/Night
7 Nights - $2,872
House
9.0
(
25 Reviews
)
4 Bedrooms
2 Bathrooms
12 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $409
/Night
7 Nights - $2,865
Cabin
10.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
7 Guests
-
Air Conditioner
-
Pet Friendly
-
Laundry
-
Bedding/Linens
US $165
/Night
7 Nights - $1,155
House
9.8
(
59 Reviews
)
2 Bedrooms
1 Bathroom
7 Guests
1400 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $351
/Night
7 Nights - $2,454
See More Pet-Friendly Vacation Rentals in Windsor on PetFriendly.io
Large Vacation Homes & Villas in Windsor
Over 5+
Large Vacation Homes & Villas in or Near Windsor
House
9.6
(
5 Reviews
)
1 Bedroom
2 Bathrooms
12 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $218
/Night
7 Nights - $1,524
House
4 Bedrooms
3 Bathrooms
10 Guests
2002.09 ft²
-
Private Beach -
Parking
-
Skiing
-
Ocean View
US $367
/Night
7 Nights - $2,569
House
3 Bedrooms
3 Bathrooms
10 Guests
-
Air Conditioner
-
Pet Friendly
-
Child Friendly
-
Laundry
US $750
/Night
7 Nights - $5,250
House
5 Bedrooms
3 Bathrooms
16 Guests
2884.73 ft²
-
Parking
-
Balcony/Terrace
-
View
-
Air Conditioner
US $365
/Night
7 Nights - $2,553
House
1 Bedroom
2 Bathrooms
12 Guests
1420.84 ft²
-
Parking
-
Internet
-
Pet Friendly
-
Sports/Activities
US $288
/Night
7 Nights - $2,018
See More Family Vacation Rentals in Windsor on FVR
Wheelchair Accessible Vacation Homes in Windsor
Over 1+
Wheelchair Accessible Vacation Homes in or Near Windsor
House
5.0
(
4 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Balcony/Terrace
-
Kitchen
-
Pet Friendly
-
Wheelchair Accessible
US $265
/Night
7 Nights - $1,855
Windsor Vacation Rentals and Airbnb Places to Stay Under $200
Over 9+
Windsor Vacation Rentals and Airbnb Places to Stay Under $200
Bed & Breakfast
9.8
(
7 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
214 ft²
-
Kitchen
-
Air Conditioner
-
TV -
Bedding/Linens
US $135
/Night
7 Nights - $945
House
7.4
(
10 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $180
/Night
7 Nights - $1,260
House
5.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
2500 ft²
-
Kitchen
-
Air Conditioner
-
Child Friendly
-
TV
US $77
/Night
7 Nights - $539
US $130
/Night
7 Nights - $910
Cottage
9.6
(
7 Reviews
)
4 Bedrooms
1 Bathroom
4 Guests
1600 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $195
/Night
7 Nights - $1,367
Ski Chalet
2 Bedrooms
1 Bathroom
4 Guests
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $147
/Night
7 Nights - $1,029
House
1 Bedroom
1 Bathroom
4 Guests
880 ft²
-
View
-
Kitchen
-
Child Friendly
-
Laundry
US $120
/Night
7 Nights - $840
Cabin
2 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $93
/Night
7 Nights - $650
See More Windsor Vacation Rental Deals
Instantly Bookable Vacation Homes in Windsor
Over 11+
Instantly Bookable Vacation Homes in or Near Windsor
Cottage
9.0
(
2 Reviews
)
4 Bedrooms
1 Bathroom
6 Guests
-
Internet
-
Child Friendly
-
Laundry
-
Bedding/Linens
US $244
/Night
7 Nights - $1,710
New
House
2 Bedrooms
1 Bathroom
5 Guests
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $363
/Night
7 Nights - $2,544
House
2 Bedrooms
1 Bathroom
8 Guests
1496 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $356
/Night
7 Nights - $2,491
House
2 Bedrooms
1 Bathroom
6 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $346
/Night
7 Nights - $2,419
Cabin
10.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
7 Guests
1203 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $338
/Night
7 Nights - $2,367
House
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $267
/Night
7 Nights - $1,870
House
9.4
(
6 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
947 ft²
-
Child Friendly
US $327
/Night
7 Nights - $2,286
Condo
9.0
(
7 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
800 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $224
/Night
7 Nights - $1,571
See More Windsor Short-Term Vacation Rentals
About Windsor Vacation Rentals
With more than 65 Windsor vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas 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 Windsor.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Windsor, 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 Windsor. Places to stay near Windsor are 761.51 ft² on average, with prices averaging US $373 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Windsor 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 Windsor
| Type | Count |
|---|---|
| Vacation Homes | 39 |
| Cabin Rentals | 13 |
| Cottages | 8 |
| Ski Chalet Rentals | 2 |
| B&B | 1 |
| Others | 1 |
Use these Quick Filters to Find a Vacation Rental in Windsor
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas 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 Windsor.
Weather in Windsor
View the weather forecast for Windsor before booking your Windsor 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 Windsor, NH
Estiavillas offers a large selection of top attractions around Windsor. Research things to do on your vacation before you visit Windsor.
Pats Peak
Keene State College
Lake Sunapee
Mount Sunapee
Crotched Mountain Ski and Ride Area
Colby-Sawyer College
Monadnock State Park
Peterborough Players
Granite Gorge
Colonial Theatre
New London Barn Playhouse
Newport Golf Club
Peterborough Town House
Brentwood Golf Course
Connecticut Lakes Region
Newport Historical Society
Central Square
Greenfield State Park
Sharon Arts Center
New London Historical Society
Windsor Vacation Rental Frequently Asked Questions
Which vacation homes in Windsor are best for families?
If you are looking for a family-friendly vacation home in Windsor, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windsor:
How many vacation rentals are available in Windsor?
Currently, the total number of properties listed in 2026 is over 65 in the Windsor area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Windsor.
