Winsor Vacation Rentals

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Our top choices for Winsor vacation rentals

room2 Southampton Hometel

room2 Southampton Hometel
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,196 reviews)
"Great location and vibe"
United Kingdom
Paul
The price is CA $116
CA $139 total
includes taxes & fees
Feb 22 - Feb 23
room2 Southampton Hometel

Adorable 2-bedroom apartment in Southampton

Adorable 2-bedroom apartment in Southampton
Freemantle
10.0 out of 10, Exceptional, (2 reviews)
"Apartment was in great condition, no complaints!"
United Kingdom
Bethany M.
The price is CA $291
CA $373 total
includes taxes & fees
Feb 14 - Feb 15
Adorable 2-bedroom apartment in Southampton

5 Yarmouth Cottages

5 Yarmouth Cottages
3.5 star property
Freshwater
9.4 out of 10, Exceptional, (3 reviews)
"Convenient and spotlessly clean small cottage is a great base for exploring the IoW. Only slight downside is that the proximity to other guests means sitting outside can be a little bit of an exercise in hearing other people’s conversation! This small point aside, can recommend for a short stay. "
United Kingdom
Clive
The price is CA $551
CA $662 total
includes taxes & fees
Feb 15 - Feb 16
5 Yarmouth Cottages

The Cliff House Hotel

The Cliff House Hotel
4.0 star property
New Milton
9.4 out of 10, Exceptional, (409 reviews)
"Room and staff excellent enjoyed our stay food good"
United Kingdom
Keith
The price is CA $199
CA $238 total
includes taxes & fees
Feb 13 - Feb 14
The Cliff House Hotel

Coventry Road Studio Flat

Coventry Road Studio Flat
2.0 star property
The Polygon
The price is CA $80
CA $97 total
includes taxes & fees
Feb 15 - Feb 16
Coventry Road Studio Flat

Peartree Serviced Apartments

Peartree Serviced Apartments
3.5 star property
Salisbury
9.6 out of 10, Exceptional, (308 reviews)
"Enjoyable stay, handy to Salisbury landmarks."
Australia
Heather
The price is CA $170
CA $205 total
includes taxes & fees
Mar 2 - Mar 3
Peartree Serviced Apartments

Large Sea View 2 bedroom Sleeps 6 - Free Parking

Large Sea View 2 bedroom Sleeps 6 - Free Parking
Bournemouth
8.8 out of 10, Excellent, (3 reviews)
"Lovely clean appt with great views and literally a hop across the road to the beach. Rooms were very nice and amenties provided which was a nice touch. Parking was easy and appt is located within easy drive of natural attractions such as Durdle Door and Sand banks if thats your interest. "
United States
Nizar S.
The price is CA $128
CA $248 total
includes taxes & fees
Feb 16 - Feb 17
Large Sea View 2 bedroom Sleeps 6 - Free Parking

The South Coast Snug

The South Coast Snug
2.0 star property
Fareham
The price is CA $125
CA $150 total
includes taxes & fees
Mar 15 - Mar 16
The South Coast Snug

Daisy Haven in Southampton

Daisy Haven in Southampton
2.0 star property
Bassett Green
The price is CA $195
CA $235 total
includes taxes & fees
Feb 23 - Feb 24
Daisy Haven in Southampton

modern Bungalow with hot tub, garden, bbq & Netflix 10 min drive to city centre

modern Bungalow with hot tub, garden, bbq & Netflix 10 min drive to city centre
Southampton
10.0 out of 10, Exceptional, (3 reviews)
"The accommodation was very comfortable and perfectly situated for a pre cruise stay! The beds were comfortable and the kitchen was very well equipped! Comfy sofas in the lounge and great internet! Highly recommended! Would definitely book again! Great host too! "
United Kingdom
Michael H.
The price is CA $233
CA $390 total
includes taxes & fees
Feb 13 - Feb 14
modern Bungalow with hot tub, garden, bbq & Netflix 10 min drive to city centre

Beautiful 2 bedroom near the sea with free parking

Beautiful 2 bedroom near the sea with free parking
Bournemouth
10.0 out of 10, Exceptional, (1 review)
"Had a lovely stay here. The appartment was great for what we needed. The location was perfect, beach at the end of the street and a nice pub! Short walk back into the main street for the shops. Only issue, there were no curtains/blinds up in the living room, didn't really bother us as not really overlooked. Apart from that would definitely stay here again."
United Kingdom
tracey f.
The price is CA $150
CA $270 total
includes taxes & fees
Feb 15 - Feb 16
Beautiful 2 bedroom near the sea with free parking

Pinnacle Suites

Pinnacle Suites
3.0 star property
Cowes
9.8 out of 10, Exceptional, (25 reviews)
"Great place to stay. Facilities are very nice and clean. Zoe is a very helpful and kind host. "
Denmark
Sebastian
The price is CA $191
CA $230 total
includes taxes & fees
Feb 20 - Feb 21
Pinnacle Suites

6 Yarmouth Cottages

6 Yarmouth Cottages
3.0 star property
Freshwater
8.0 out of 10, Very good, (4 reviews)
"A very pleasant place to stay in a lovely location on the western side of the island. It has lovely views over fields. The cottage was clean and well equipped. The bed was comfortable and the bathrooms and shower were of good quality. The owner was both friendly and helpful. Thank you :-)"
United Kingdom
Adam
The price is CA $551
CA $662 total
includes taxes & fees
Mar 14 - Mar 15
6 Yarmouth Cottages

4thedome

4thedome
3.5 star property
New Milton
9.4 out of 10, Exceptional, (12 reviews)
"Had a lovely stay in this apartment . It was excellent. Very very clean and comfortable, with everything you could need and a lot of little extras. Just a couple of steps over to the clifftop in Barton on sea. Would definitely stay again."
United Kingdom
Stephen
The price is CA $154
CA $249 total
includes taxes & fees
Feb 15 - Feb 16
4thedome

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, (10 reviews)
"Lovely 1 night stay in beautiful location. Louise very welcoming and property was perfect and very clean."
United Kingdom
Emily S.
The price is CA $308
CA $348 total
includes taxes & fees
Feb 13 - Feb 14
Farm Cottage on a Secluded 9-acre Equestrian Small Holding

3 Bedrooms house ideal for long Stays!

3 Bedrooms house ideal for long Stays!
Southampton
10.0 out of 10, Exceptional, (3 reviews)
"Great location, lovely clean property can recommend."
United Kingdom
Michael R.
The price is CA $183
CA $302 total
includes taxes & fees
Feb 17 - Feb 18
3 Bedrooms house ideal for long Stays!

Romantic Swiss Cabin Hideaway & Hot Tub Spa Pool

Romantic Swiss Cabin Hideaway & Hot Tub Spa Pool
Chandler's Ford
The price is CA $118
CA $176 total
includes taxes & fees
Feb 23 - Feb 24
Romantic Swiss Cabin Hideaway & Hot Tub Spa Pool

Charles Hope Salisbury Centre

Charles Hope Salisbury Centre
3.5 star property
Salisbury
9.6 out of 10, Exceptional, (5 reviews)
"Great location and well appointed apartment"
Australia
Greg
Charles Hope Salisbury Centre

The Stables, Wickham - a barn conversion that sleeps 2 guests in 1 bedroom

The Stables, Wickham - a barn conversion that sleeps 2 guests in 1 bedroom
Shedfield
9.8 out of 10, Exceptional, (10 reviews)
"Fabulous place to stay."
United States
CHRISTOPHER S.
The price is CA $778
CA $778 total
includes taxes & fees
Feb 20 - Feb 21
The Stables, Wickham - a barn conversion that sleeps 2 guests in 1 bedroom

The Annex Ferndown

The Annex Ferndown
Ferndown
8.6 out of 10, Excellent, (7 reviews)
"I plan to stay here again the next time I come to Ferndown. Great location, small but perfectly designed space, very comfortable and well equipped. Comfortable beds."
United States
claire c.
The price is CA $166
CA $388 total
includes taxes & fees
Mar 1 - Mar 2
The Annex Ferndown
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

Find out more about Winsor

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winsor. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.