Estia Villas - Vacation Rentals in Winsor
Cottage
9.4
(
119 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Fireplace/Heating -
Balcony/Terrace -
Pet Friendly -
Kitchen
US $286
/Night
7 Nights - $1,999
10.0
(
3 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
-
Fireplace/Heating
-
View -
Parking -
Internet
US $432
/Night
7 Nights - $3,021
9.2
(
153 Reviews
)
1 Bedroom
1 Bathroom
-
Breakfast -
Parking
-
Internet
-
Child Friendly
US $173
/Night
7 Nights - $1,214
Cottage
10.0
(
5 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
-
Hot Tub -
Fireplace/Heating
-
Ocean View -
Balcony/Terrace
US $467
/Night
7 Nights - $3,269
House
10.0
(
2 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $403
/Night
7 Nights - $2,820
Cottage
10.0
(
2 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
1292 ft²
-
Fireplace/Heating
-
Kitchen
-
Parking
-
Internet
US $223
/Night
7 Nights - $1,564
House
10.0
(
1 Review
)
4 Bedrooms
3 Bathrooms
8 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $1,362
/Night
7 Nights - $9,532
House
10.0
(
1 Review
)
5 Bedrooms
2 Bathrooms
9 Guests
-
Spa -
Fireplace/Heating
-
Pet Friendly
-
Kitchen
US $559
/Night
7 Nights - $3,916
See More Winsor Vacation Rentals
Luxury Places to Stay in Winsor
Over 84+
Luxury Places to Stay in or Near Winsor
9.7
(
10 Reviews
)
4 Bedrooms
4 Bathrooms
14 Guests
3196.88 ft²
-
Hot Tub
-
Fireplace/Heating
-
Balcony/Terrace
-
View
US $1,303
/Night
7 Nights - $9,124
House
8.8
(
5 Reviews
)
4 Bedrooms
4 Bathrooms
10 Guests
-
Balcony/Terrace
-
Child Friendly
-
Laundry -
TV
US $1,249
/Night
7 Nights - $8,742
House
9.4
(
3 Reviews
)
5 Bedrooms
3 Bathrooms
10 Guests
-
Hot Tub
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
US $1,051
/Night
7 Nights - $7,355
7.3
(
3 Reviews
)
4 Bedrooms
3 Bathrooms
9 Guests
1108.68 ft²
-
Fireplace/Heating
-
Pet Friendly
-
Parking
-
Child Friendly
US $1,035
/Night
7 Nights - $7,245
Apartment
8.0
(
1 Review
)
4 Bedrooms
1 Bathroom
16 Guests
-
Kitchen
-
Child Friendly
-
Laundry
-
Barbecue/Outdoor Cooking
US $903
/Night
7 Nights - $6,323
8.6
(
5 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
861.11 ft²
-
Balcony/Terrace
-
View
-
Parking
-
Internet
US $623
/Night
7 Nights - $4,361
8.0
(
2 Reviews
)
5 Bedrooms
3 Bathrooms
12 Guests
1797.57 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
View
-
Pet Friendly
US $581
/Night
7 Nights - $4,064
House
4 Bedrooms
1 Bathroom
8 Guests
2368 ft²
-
Fireplace/Heating
-
Pet Friendly
-
Kitchen
-
Parking
US $572
/Night
7 Nights - $4,005
See More Winsor Luxury Vacation Rentals
Find More Winsor Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Winsor
Over 3+
Top-Rated Vacation Rentals with a Pool in or Near Winsor
7.6
(
282 Reviews
)
1 Bathroom
-
Fireplace/Heating
-
Pool -
Balcony/Terrace
-
Breakfast
US $179
/Night
7 Nights - $1,252
7.1
(
923 Reviews
)
8 Bathrooms
205.86 ft²
-
Private Pool -
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $183
/Night
7 Nights - $1,284
Other
10.0
(
4 Reviews
)
4 Bedrooms
4 Bathrooms
14 Guests
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $1,080
/Night
7 Nights - $7,563
See More Winsor Vacation Rentals with a Pool
Pet-Friendly Vacation Rentals in Winsor
Over 30+
Pet-Friendly Vacation Rentals in or Near Winsor
House
10.0
(
1 Review
)
2 Bedrooms
1 Bathroom
4 Guests
1561 ft²
-
Fireplace/Heating
-
Pet Friendly
-
Kitchen
-
Parking
US $392
/Night
7 Nights - $2,745
House
10.0
(
1 Review
)
5 Bedrooms
3 Bathrooms
10 Guests
-
View
-
Pet Friendly
-
Parking
-
Internet
US $504
/Night
7 Nights - $3,531
House
10.0
(
1 Review
)
3 Bedrooms
1 Bathroom
5 Guests
-
Hot Tub
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
US $313
/Night
7 Nights - $2,188
House
1 Bedroom
1 Bathroom
3 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $305
/Night
7 Nights - $2,137
House
2 Bedrooms
1 Bathroom
4 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $229
/Night
7 Nights - $1,606
Cottage
9.2
(
29 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $155
/Night
7 Nights - $1,085
House
10.0
(
1 Review
)
2 Bedrooms
1 Bathroom
4 Guests
560 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $144
/Night
7 Nights - $1,006
Cottage
10.0
(
1 Review
)
2 Bedrooms
1 Bathroom
2 Guests
-
Fireplace/Heating
-
Pet Friendly
-
Kitchen
-
Parking
US $106
/Night
7 Nights - $740
See More Pet-Friendly Vacation Rentals in Winsor on PetFriendly.io
Large Vacation Homes & Villas in Winsor
Over 5+
Large Vacation Homes & Villas in or Near Winsor
Cottage
5 Bedrooms
3 Bathrooms
8 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $593
/Night
7 Nights - $4,150
9.3
(
150 Reviews
)
11 Bedrooms
11 Bathrooms
22 Guests
215.28 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
View
-
Breakfast
US $134
/Night
7 Nights - $938
8.6
(
308 Reviews
)
5 Bedrooms
5 Bathrooms
12 Guests
182.99 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
View
-
Pet Friendly
US $80
/Night
7 Nights - $558
Other
9.1
(
55 Reviews
)
5 Bedrooms
4 Bathrooms
10 Guests
243.26 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
View
-
Pet Friendly
US $184
/Night
7 Nights - $1,288
See More Family Vacation Rentals in Winsor on FVR
Wheelchair Accessible Vacation Homes in Winsor
Over 3+
Wheelchair Accessible Vacation Homes in or Near Winsor
8.3
(
1063 Reviews
)
4 Bathrooms
296.01 ft²
-
Spa
-
Fireplace/Heating
-
Balcony/Terrace
-
View
US $171
/Night
7 Nights - $1,200
10.0
(
1 Review
)
1 Bathroom
-
Breakfast
-
Parking
-
Internet
-
Child Friendly
US $151
/Night
7 Nights - $1,055
8.3
(
590 Reviews
)
4 Bathrooms
134.55 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
View
-
Breakfast
US $132
/Night
7 Nights - $921
Winsor Vacation Rentals and Airbnb Places to Stay Under $200
Over 32+
Winsor Vacation Rentals and Airbnb Places to Stay Under $200
Cottage
9.6
(
47 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $108
/Night
7 Nights - $756
9.6
(
170 Reviews
)
3 Bedrooms
2 Bathrooms
4 Guests
209.89 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
View
-
Parking
US $65
/Night
7 Nights - $455
9.0
(
113 Reviews
)
1 Bathroom
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $113
/Night
7 Nights - $790
Apartment
1 Bedroom
1 Bathroom
2 Guests
-
Fireplace/Heating
-
Internet
-
TV
-
Bedding/Linens
US $115
/Night
7 Nights - $805
Apartment
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
5 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $163
/Night
7 Nights - $1,144
House
3 Bedrooms
2 Bathrooms
6 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $195
/Night
7 Nights - $1,364
Apartment
3 Bedrooms
1 Bathroom
6 Guests
-
Fireplace/Heating
-
Kitchen
-
Child Friendly
-
Laundry
US $186
/Night
7 Nights - $1,300
US $182
/Night
7 Nights - $1,272
See More Winsor Vacation Rental Deals
Instantly Bookable Vacation Homes in Winsor
Over 14+
Instantly Bookable Vacation Homes in or Near Winsor
Cottage
9.6
(
44 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $115
/Night
7 Nights - $805
House
10.0
(
1 Review
)
4 Bedrooms
2 Bathrooms
9 Guests
1109 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $361
/Night
7 Nights - $2,530
House
10.0
(
1 Review
)
2 Bedrooms
1 Bathroom
4 Guests
-
Hot Tub
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
US $266
/Night
7 Nights - $1,865
Cottage
3 Bedrooms
2 Bathrooms
6 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $393
/Night
7 Nights - $2,752
New
House
1 Bedroom
1 Bathroom
4 Guests
-
Hot Tub
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
US $350
/Night
7 Nights - $2,449
Cottage
2 Bedrooms
2 Bathrooms
4 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $330
/Night
7 Nights - $2,307
Cottage
3 Bedrooms
1 Bathroom
6 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $314
/Night
7 Nights - $2,198
Cottage
10.0
(
4 Reviews
)
3 Bedrooms
2 Bathrooms
9 Guests
1109 ft²
-
Hot Tub
-
Fireplace/Heating
-
Ocean View
-
Balcony/Terrace
US $472
/Night
7 Nights - $3,303
See More Winsor Short-Term Vacation Rentals
About Winsor Vacation Rentals
With more than 93 Winsor 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 Winsor.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Winsor, 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 Winsor. Places to stay near Winsor are 657.46 ft² on average, with prices averaging US $322 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Winsor 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 Winsor
| Type | Count |
|---|---|
| Vacation Homes | 42 |
| Cottages | 16 |
| Holiday Apartments | 12 |
| Hotels | 11 |
| B&B | 4 |
| Others | 3 |
Use these Quick Filters to Find a Vacation Rental in Winsor
★ 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 Winsor.
Weather in Winsor
View the weather forecast for Winsor before booking your Winsor Vacation Rentals to confirm your best time to go.
December - February
High 43°F Low 32°F
March - May
High 61°F Low 36°F
June - August
High 63°F Low 48°F
September - November
High 58°F Low 35°F
Top Attractions Around Winsor, GB
Estiavillas offers a large selection of top attractions around Winsor. Research things to do on your vacation before you visit Winsor.
Southampton Cruise Terminal
Paultons Family Theme Park - Home of Peppa Pig World
Winchester Cathedral
Marwell Zoo
University of Southampton
WestQuay Shopping Centre
Mayflower Theatre
Southampton Solent University
Salisbury Cathedral
Osborne House
Beaulieu National Motor Museum
University of Winchester
St. Mary's Stadium
O2 Academy Bournemouth
Christchurch Harbour
Ocean Village Marina
Ageas Bowl Cricket Ground
Seaclose Park
Lymington Pier Ferry Port
Winchester Guildhall
Winsor Vacation Rental Frequently Asked Questions
Which vacation homes in Winsor are best for families?
If you are looking for a family-friendly vacation home in Winsor, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winsor:
How many vacation rentals are available in Winsor?
Currently, the total number of properties listed in 2026 is over 93 in the Winsor area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Winsor.
