A forested area with a dirt path, tall trees, and dense underbrush.

Winsor Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Winsor vacation rentals

Interior entrance

1. Second Nature Southampton

Second Nature Southampton
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,308 reviews)
"Great place to stay on the way to our cruise…would definitely recommend!!"
Canada
Shelly
$111 nightly
The price is $133
Aug 31 - Sep 1
Total with taxes and fees
Second Nature Southampton
Deluxe Studio

2. Settle Southampton

Settle Southampton
2.0 star property
Freemantle
8.8 out of 10, Excellent, (8 reviews)
"Brilliant property really well situated for the centre of town. Deffo coming back."
United Kingdom
Chris
$96 nightly
The price is $115
Aug 31 - Sep 1
Total with taxes and fees
Settle Southampton
Deluxe Apartment

3. QE2 Loft Apartments

QE2 Loft Apartments
3.0 star property
Southampton City Centre
6.4 out of 10, (8 reviews)
"No Air conditioning! Bar under with loud party all night long. Windows open for air. You book this room only if you want to party. Otherwise you will be kept up all night long. 90 degrees outside and hotter inside do to restaurant ovens directly under room. It was the worst experience. Jet lag turned into nightmare 😫"
United States
BRIAN
$178 nightly
The price is $213
Aug 28 - Aug 29
Total with taxes and fees
QE2 Loft Apartments
Lobby sitting area

4. For Students Only Abodus The Walls Southampton - Campus Accommodation

For Students Only Abodus The Walls Southampton - Campus Accommodation
2.0 star property
Southampton City Centre
5.8 out of 10, (9 reviews)
"It was ok for a quick stay. nothing fancy. "
United States
Lamel
For Students Only Abodus The Walls Southampton - Campus Accommodation
Private kitchen

5. Adorable 2-bedroom apartment in Southampton

Adorable 2-bedroom apartment in Southampton
Freemantle
9.0 out of 10, Wonderful, (4 reviews)
"Apartment was in great condition, no complaints!"
United Kingdom
Bethany M.
$252 nightly
The price is $252
Aug 29 - Aug 30
Total with taxes and fees
Adorable 2-bedroom apartment in Southampton
Exterior

6. Farm Cottage on a Secluded 9-acre Equestrian Small Holding

Farm Cottage on a Secluded 9-acre Equestrian Small Holding
Salisbury
10.0 out of 10, Exceptional, (15 reviews)
"Louise was fantastic, we had to stay an extra night and the communication was easy and great. Would recommend."
United States
Jordan J.
$238 nightly
The price is $238
Sep 16 - Sep 17
Total with taxes and fees
Farm Cottage on a Secluded 9-acre Equestrian Small Holding
Miscellaneous

7. Bayview Apartments

Bayview Apartments
2.0 star property
Southampton City Centre
8.0 out of 10, Very Good, (5 reviews)
"The apartment was reasonably priced, conveniently located to our destination and perfectly adequate for our needs."
United States
Donald
$182 nightly
The price is $218
Aug 31 - Sep 1
Total with taxes and fees
Bayview Apartments
Exterior

8. Radstock Road - Room 4a

Radstock Road - Room 4a
Southampton
$74 nightly
The price is $88
Aug 31 - Sep 1
Total with taxes and fees
Radstock Road - Room 4a
Exterior

9. 1 bedroom accommodation in Burgate, near Fordingbridge

1 bedroom accommodation in Burgate, near Fordingbridge
Burgate, near Fordingbridge
9.0 out of 10, Wonderful, (21 reviews)
"Lovely place to stay - comfortable and well equipped. Ideal location."
United Kingdom
Ruth P.
$266 nightly
The price is $266
Sep 11 - Sep 12
Total with taxes and fees
1 bedroom accommodation in Burgate, near Fordingbridge
Private kitchen

10. Centrally located double room

Centrally located double room
Freemantle
$44 nightly
The price is $52
Sep 6 - Sep 7
Total with taxes and fees
Centrally located double room
Outdoor dining

11. New Forest National Park Studio @Forest Palms

New Forest National Park Studio @Forest Palms
Hyde
10.0 out of 10, Exceptional, (10 reviews)
"We had a fabulous time at New Forest Palms. Super clean and modern apartment with all you need nearby! Pubs, food, wild horses. 😊"
United Kingdom
Hazel D.
$240 nightly
The price is $240
Sep 1 - Sep 2
Total with taxes and fees
New Forest National Park Studio @Forest Palms
Private kitchen

12. Beautiful 2 bedroom full-furnished semi-detached house with parking

Beautiful 2 bedroom full-furnished semi-detached house with parking
Dibden Purlieu
9.6 out of 10, Exceptional, (13 reviews)
"Accommodation was beautifully clean and well equipped in a great location. "
United Kingdom
Julie P.
$197 nightly
The price is $197
Sep 6 - Sep 7
Total with taxes and fees
Beautiful 2 bedroom full-furnished semi-detached house with parking
Dining

13. 3 Bedrooms house ideal for long Stays!

3 Bedrooms house ideal for long Stays!
Southampton
10.0 out of 10, Exceptional, (4 reviews)
"Great location, lovely clean property can recommend."
United Kingdom
Michael R.
$290 nightly
The price is $290
Sep 9 - Sep 10
Total with taxes and fees
3 Bedrooms house ideal for long Stays!
Terrace/patio

14. Luxury shepherd's hut

Luxury shepherd's hut
Bransgore
9.8 out of 10, Exceptional, (43 reviews)
"We had the best stay in this beautiful shepherds hut. The location was perfect, the position of the shepherds hut allowed for guest privacy while also offering wonderful views and outdoor space. The accommodation was perfect with everything you could need. Would highly recommend. "
United Kingdom
Hayley M.
$238 nightly
The price is $238
Aug 27 - Aug 28
Total with taxes and fees
Luxury shepherd's hut
Double Room

15. Settle Winchester

Settle Winchester
2.0 star property
Winchester
$110 nightly
The price is $132
Sep 6 - Sep 7
Total with taxes and fees
Settle Winchester
Room

16. The Bike Shed

The Bike Shed
3.0 star property
Romsey
$466 nightly
The price is $559
Sep 13 - Sep 14
Total with taxes and fees
The Bike Shed
Exclusive Apartment, Private Bathroom | Interior

17. 4thedome

4thedome
3.5 star property
New Milton
9.4 out of 10, Exceptional, (13 reviews)
"Excellent, will definitely be back, bedding and towels provided, great location, excellent communication "
United Kingdom
Claire
$184 nightly
The price is $212
Aug 31 - Sep 1
Total with taxes and fees
4thedome
Room

18. 1 Bed Flat - Sleeps 2 - Parking - Wifi

1 Bed Flat - Sleeps 2 - Parking - Wifi
3.0 star property
The Polygon
$526 nightly
The price is $631
Sep 1 - Sep 2
Total with taxes and fees
1 Bed Flat - Sleeps 2 - Parking - Wifi
Exterior

19. A stroll to Ringwood, near to New Forest & South Coast Beaches. Private Parking

A stroll to Ringwood, near to New Forest & South Coast Beaches. Private Parking
Ringwood
10.0 out of 10, Exceptional, (13 reviews)
"very modern and clean accommodation local to shops and bars"
United Kingdom
Donna E.
$310 nightly
The price is $310
Sep 17 - Sep 18
Total with taxes and fees
A stroll to Ringwood, near to New Forest & South Coast Beaches. Private Parking
Beach

20. Unique detached holiday cottage, Hampshire

Unique detached holiday cottage, Hampshire
Sopley
9.8 out of 10, Exceptional, (83 reviews)
"Great place for a short stay"
United Kingdom
Keiron D.
$232 nightly
The price is $232
Sep 7 - Sep 8
Total with taxes and fees
Unique detached holiday cottage, Hampshire
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winsor Hotel Reviews

The Crown Manor House Hotel

The Crown Manor House Hotel

8/10 Good
"A bit too quirky for us."
Pantelitsa 1-night trip
Posted 2 hours ago
The Crown Manor House Hotel

Find out more about Winsor

Everything you need to know about Winsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $115 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winsor rentals

At Expedia, we put the best Winsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Winsor?

Yes, we give you a choice of vacation rentals close to the most popular sights in Winsor, or you can select a more remote option if you're looking for relaxation.

What are some of the best vacation home rentals that Winsor has to offer?

Four Corners Holiday Home with Hot Tub & Sauna: You might want to consider this vacation home rental near Winsor, which is located near the airport and has a furnished patio, a private yard, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and an oven, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

What can I see and do in Winsor?

While exploring the area, visit family-friendly sights like Paultons Family Theme Park - Home of Peppa Pig World, or get outside and enjoy nature at New Forest National Park. Southampton Cruise Terminal and New Forest Wildlife Park are a couple of places you'll find in the larger area.

What are vacation rentals like in Winsor?

Vacation rentals are private properties you can book for several days or longer in Winsor. Vacation rentals offer extras such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a small group gathering.