Winsor Vacation Rentals

Start date: Check-in selected.
End date: Check-out
    bundle and save illustration

    Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
    one key illustration

    OneKeyCash

    Earn OneKeyCash on all your eligible bookings
    ftc illustration

    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 19 - Sep 21
In two months
Oct 31 - Nov 2
In three months
Nov 28 - Nov 30
In four months
Dec 26 - Dec 28

Vacation Rentals in Winsor

room2 Southampton Hometel
Front of property

room2 Southampton Hometel

4.0 star property
9.4 out of 10, Exceptional, (1083)
"Clean, with friendly staff. Within walking distance to local eateries and grocery."
$102 nightly
The price is $122
Sep 4 - Sep 5
Total with taxes and fees
room2 Southampton Hometel
Southampton Serviced Apartment
Balcony view

Southampton Serviced Apartment

4.0 star property
8.4 out of 10, Very Good, (171)
"It was in a good location. The communication was perfect. "
Southampton Serviced Apartment
The Cliff House Hotel
Exterior

The Cliff House Hotel

4.0 star property
9.4 out of 10, Exceptional, (392)
"Really comfortable room, excellent food in restaurant, good parking and pleasant and friendly staff"
$191 nightly
The price is $230
Sep 5 - Sep 6
Total with taxes and fees
The Cliff House Hotel
The Madison
Superior Studio | 1 bedroom, premium bedding, individually decorated

The Madison

3.0 star property
9.4 out of 10, Exceptional, (26)
"Stunning property, host was lovely very accomodating quick to respond, would definitely use again, we were working from early hours to late eveming so didn't have chance to shop or eat oit on thia occasion but judging by everything else this host and property offered i would give 10 out of 10 on all "
The Madison
Luxury villa, amazing location, pool, jacuzzi, snooker, cinema & tennis court!
Outdoor pool, a heated pool

Luxury villa, amazing location, pool, jacuzzi, snooker, cinema & tennis court!

10.0 out of 10, Exceptional, (47)
"Fantastic stay in the new forest. Great location, really nice property. Absolutely exceeded our expectations. Highly recommend and would stay again!"
Luxury villa, amazing location, pool, jacuzzi, snooker, cinema & tennis court!
Peartree Serviced Apartments
Studio, 1 Queen Bed | Private kitchen | Fridge, microwave, stovetop, dishwasher

Peartree Serviced Apartments

3.5 star property
9.6 out of 10, Exceptional, (284)
"We‘ve only been there for one night. In our opinion the apartment was very clean and tidy. The biggest issue was that our apartment (family apartment) had no windows in the bedrooms, so there was no possibility to get really fresh air in there. We were really happy about the little breakfast gifts they had there. "
$136 nightly
The price is $164
Sep 28 - Sep 29
Total with taxes and fees
Peartree Serviced Apartments
Chelsea Hotel
Exterior

Chelsea Hotel

3.0 star property
9.2 out of 10, Wonderful, (81)
"Room was clean and welcoming. I did like the interaction not needed to check in, smart easy and quick way of doing things. I enjoyed it! Room was exactly as stated and advertised. The only thing missing was maybe a chair to sit on. We did not miss out on anything, happy about our stay!"
$73 nightly
The price is $88
Sep 14 - Sep 15
Total with taxes and fees
Chelsea Hotel
Bayview Apartments
Shared kitchen

Bayview Apartments

2.0 star property
7.0 out of 10, Good, (2)
"To be honest although the apartment was really nice we didn’t have hardly any knives and forks and spoons for 5 people, the fridge was filthy and the cooking equipment was old worn out and filthy. For nearly £300 for one night we expected better "
$180 nightly
The price is $216
Sep 10 - Sep 11
Total with taxes and fees
Bayview Apartments
Pinnacle Suites
Deluxe Room, 1 Double Bed, Harbor View | 1 bedroom, premium bedding, Select Comfort beds, desk

Pinnacle Suites

3.0 star property
9.8 out of 10, Exceptional, (22)
"If I could rate it higher I would. Super friendly, great location, very comfortable rooms (even with AC, a big plus!)"
$144 nightly
The price is $173
Oct 1 - Oct 2
Total with taxes and fees
Pinnacle Suites
The Walls
Lobby sitting area

The Walls

2.0 star property
4.6 out of 10, (7)
"It was ok for a quick stay. nothing fancy. "
The Walls
Charming 2-bed Apartment in Central Southampton
Apartment | Private kitchen | Fridge, microwave, oven, stovetop

Charming 2-bed Apartment in Central Southampton

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great apartment, super friendly host!"
$281 nightly
The price is $338
Oct 2 - Oct 3
Total with taxes and fees
Charming 2-bed Apartment in Central Southampton
Luxury villa for 22 people with pool, jacuzzi, large garden and private pub!
Fridge, microwave, oven, stovetop

Luxury villa for 22 people with pool, jacuzzi, large garden and private pub!

9.8 out of 10, Exceptional, (188)
"We had the most wonderful last minute stay. timo was very helpful, available and accomodating. The venue was perfect - spotless and welcoming. Very spacious and beautiful inside and outside, with lovely thoughtful touches. None of us wanted to leave! Thank you Timo"
Luxury villa for 22 people with pool, jacuzzi, large garden and private pub!
Bournemouth Getaway for 14
Fridge, microwave, oven, stovetop

Bournemouth Getaway for 14

9.0 out of 10, Wonderful, (4)
"The house was very spacious, clean and well equipped for our group of 12 and 2 dogs. We had no issues with our stay. I would highly recommend, we had a brilliant time. Thanks Kim"
Bournemouth Getaway for 14
Superyacht on 5* Ocean Village Marina, Southampton
Marina

Superyacht on 5* Ocean Village Marina, Southampton

9.6 out of 10, Exceptional, (7)
"The yacht Ohana is a great place to stay with excellent facilities and in a fab location close to bars and restaurants.A very helpful owner made our weekend perfect! "
$389 nightly
The price is $389
Sep 4 - Sep 5
Total with taxes and fees
Superyacht on 5* Ocean Village Marina, Southampton
Beautiful 2 bedroom full-furnished semi-detached house with parking
Fridge, microwave, oven, dishwasher

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

9.4 out of 10, Exceptional, (6)
"Everything was perfect!"
$205 nightly
The price is $205
Sep 4 - Sep 5
Total with taxes and fees
Beautiful 2 bedroom full-furnished semi-detached house with parking
Premium Double Room with Ensuite
Beach

Premium Double Room with Ensuite

2.0 star property
2.0 out of 10, (1)
"Be very very careful when choosing this flat! The pictures do not match the accommodation at all. The cleanliness leaves much to be desired, the conditions are non-existent and the owner does not inspire trust or safety, as the apartment does not offer either. I do not recommend this place for women. I do not think I have ever met such an unsafe place. Avoid staying here, expedia should remove it from the site."
$240 nightly
The price is $240
Sep 4 - Sep 5
Total with taxes and fees
Premium Double Room with Ensuite
City Centre Ensuite Rooms--Landmark-Close to Docks/Stadium
Fridge, microwave, oven, coffee/tea maker

City Centre Ensuite Rooms--Landmark-Close to Docks/Stadium

$1,174 nightly
The price is $1,174
Sep 4 - Sep 5
Total with taxes and fees
City Centre Ensuite Rooms--Landmark-Close to Docks/Stadium
Southampton retreat-Hot Tub-Pool-Parking
Exterior

Southampton retreat-Hot Tub-Pool-Parking

2.0 star property
7.0 out of 10, Good, (2)
"Serene location. Nice property. "
Southampton retreat-Hot Tub-Pool-Parking
Family House in Eastleigh
House | Private kitchen | Fridge, microwave, oven, stovetop

Family House in Eastleigh

2.0 star property
Family House in Eastleigh
5-bed house: pool, tennis court, walk to beach, 10 acres
Exterior

5-bed house: pool, tennis court, walk to beach, 10 acres

10.0 out of 10, Exceptional, (68)
"A beautiful, charming and well-kept house and grounds near Yarmouth just as "
5-bed house: pool, tennis court, walk to beach, 10 acres
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winsor Hotel Reviews

Macdonald Botley Park Hotel & Spa

Macdonald Botley Park Hotel & Spa

10/10 Excellent
"Nice stay"
Simon 1-night trip
Posted 2 months ago
Macdonald Botley Park Hotel & Spa

Find out more about Winsor

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 $88 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

The Cliff House Hotel: Visitors like this Winsor vacation home rental. It offers a terrace, a garden, and daily housekeeping to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

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.