Winterslow Vacation Rentals from CA $87: Short-Term Rentals for 2026

Q: What's the top vacation rental that Winterslow has to offer?

Unique waterside home in stunning location. : This vacation home rental near Winterslow is located on the waterfront and has a balcony, a garden, and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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Our top choices for Winterslow vacation rentals

A tent with a bed inside, a colorful rug, and a sign on the ground.

1. Stone Circle Glamping

Durrington

Darnell

CA $87 total

includes taxes & fees

Oct 2 - Oct 3

A sign for Hotel Peartree, a serviced apartment, with contact information and website.

2. Peartree Serviced Apartments

Salisbury

Stephanie

CA $240 total

includes taxes & fees

Oct 4 - Oct 5

A living room with a dark blue sofa, a round wooden coffee table, a dining table with chairs, a large abstract painting, a round mirror, and a window with curtains.

3. Charles Hope Salisbury Centre

Salisbury

Theodros

CA $224 total

includes taxes & fees

Oct 11 - Oct 12

A spacious living area with a staircase, a dining table, and two sofas.

4. The Coach House Apartment — Stylish Loft Retreat for up to 4 ppl.

Clarendon

CA $378 total

includes taxes & fees

Oct 1 - Oct 2

A residential property with a large lawn, a wooden barn, and a brick house.

5. The Old Stables — Wiltshire Countryside Cottage for up to 6 ppl.

Clarendon

CA $440 total

includes taxes & fees

Oct 1 - Oct 2

A modern living room with a sofa, coffee table, and a view of the kitchen.

6. The Carriage House — Wiltshire Countryside Cottage for up to 6 ppl.

Clarendon

CA $453 total

includes taxes & fees

Oct 8 - Oct 9

A bedroom with a sloped ceiling, a heart-shaped wall decoration, a bed with white and dark pillows, and a wooden nightstand with a lamp.

7. The Summer House — Unique Hilltop Retreat for up to 4 ppl.

Salisbury

CA $474 total

includes taxes & fees

Oct 7 - Oct 8

A wooden arbor with pink blossoms, a brick pathway, and a house with a blue roof in the background.

8. Cozy & Self Contained The Garden Annex 306

Salisbury

Dala B.

CA $195 total

includes taxes & fees

Oct 20 - Oct 21

A bedroom with a bed, a nightstand, a lamp, a window with curtains, and a radiator.

9. Settle Winchester

Winchester City Center

CA $170 total

includes taxes & fees

Oct 4 - Oct 5

A row of wooden cabins with attached porches, each with a small porch light.

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

Salisbury

Diana T.

CA $289 total

includes taxes & fees

Oct 8 - Oct 9

A bedroom with a wooden door, a bed with a beige and white striped bedspread, a fluffy beige throw blanket, and a pink pillow. There are framed pictures on the wall and a window with curtains.

11. The Bike Shed

Romsey

CA $770 total

includes taxes & fees

Oct 14 - Oct 15

A paved driveway leading to a wooden gate, a bicycle with a bag, and a shed in a garden setting.

12. Beautiful New Forest Hideaway

West Wellow

Alena M.

CA $328 total

includes taxes & fees

Oct 14 - Oct 15

A modern interior with a red sofa, black chairs, and a patterned floor.

13. Second Nature Southampton

Southampton City Centre

Gary

CA $148 total

includes taxes & fees

Oct 4 - Oct 5

A traditional thatched-roof house with a brick facade, a white door, and a window.

14. 1 bedroom accommodation in Burgate, near Fordingbridge

Burgate, near Fordingbridge

Rahul Naithani

CA $366 total

includes taxes & fees

Oct 1 - Oct 2

A traditional brick house with a gabled roof, surrounded by lush greenery and flowering plants.

15. Beautiful, traditional rural cottage

Shrewton

Michael

CA $285 total

includes taxes & fees

Oct 5 - Oct 6

A compact kitchen with wooden cabinets, a built-in washing machine, a gas stove, and a tiled backsplash.

16. Ocean Quay Luxury - Stylish 2 Bed - Has Parking

Southampton City Centre

CA $227 total

includes taxes & fees

Oct 7 - Oct 8

A modern kitchen with black tiled backsplash, wooden cabinets, a Bosch refrigerator, and a built-in washing machine.

17. Coventry Road Apartments Flat 1

The Polygon

CA $101 total

includes taxes & fees

Oct 1 - Oct 2

An outdoor patio with wooden furniture, a table set for dining, and a pergola with climbing plants.

18. New Forest National Park Studio @Forest Palms

Hyde

Hazel D.

CA $300 total

includes taxes & fees

Oct 14 - Oct 15

A conservatory with a glass ceiling, a cushioned seating area, and various potted plants.

19. Annie’s House in Amesbury

Amesbury

CA $745 total

includes taxes & fees

Oct 16 - Oct 17

A cozy room with a wicker chair, a small table with a vase of flowers, and a view of a garden through large windows.

20. 2-Bed House Sleeps 4 - Enclosed Garden - Tv & WiFi

Amesbury, Salisbury

CA $695 total

includes taxes & fees

Oct 2 - Oct 3

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Top Winterslow Hotel Reviews

ibis Southampton Centre

10/10 Excellent

"Ibis was close to the cruise port and that was important for us. The hotel was comfortable and clean."

Norton Park Hotel, Spa & Manor House

8/10 Good

"We came to the Norton Park 3 years ago and returned because it was so excellent. Whereas the hotel is still amazing, standards have slipped unfortunately. There are a small number of staff that have so much potential but lack management guidance. The grounds are magnificent but the fabulous woodland walk that was there 3 years ago has become overgrown so the walks we had with our dog were contained more to the manor house and hotel which was a shame. We also missed the rope swing that hung from the bought of the tree by the pond. Would still recommend"

DoubleTree by Hilton Southampton

8/10 Good

"Beautiful property located in Chilwack, just outside the main Southampton area. The property is well maintained with well appointed rooms and amenities. Our rooms were spacious and bright, even with being located on the 1st floor. We had opted for the breakfast included rate, and thankful we were for the choice. Lovely tea, coffee, fruit, pastries, cereal as well as hot items. The hotel itself is a little outside the city centre, so a taxi is highly recommended for about 15 quid. We headed back into the city centre last night for a couple for a couple of drinks and food at the Scholars Arms. Again, great experience. Remember, you have to order at the bar as there is no table service. One single complaint about the hotel, if I may, our bed was not comfortable at all. It was like sleeping on the box spring only, as the mattress was either not existent or needed to be replaced. Otherwise, lovely!!"

Find out more about Winterslow

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 Winterslow. 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

Can I find vacation rentals in Winterslow?

Yes, we give you a choice of vacation rentals near well known points of interest in Winterslow, or you can choose a secluded option if you're looking for a relaxing stay.

What's the top vacation rental that Winterslow has to offer?

Unique waterside home in stunning location.: This vacation home rental near Winterslow is located on the waterfront and has a balcony, a garden, and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What’s there to see and do in Winterslow?

Explore the area and family-friendly sights such as Paultons Family Theme Park - Home of Peppa Pig World, or get out into nature at a spot like New Forest National Park. In the larger area, you’ll find Southampton Cruise Terminal and Boscombe Down Aviation Collection.

What’s a vacation rental in Winterslow like?

Vacation rentals are privately owned properties you can book for a couple of days or more in Winterslow. Vacation rentals feature extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for family trips.

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Check prices for these dates

Our top choices for Winterslow vacation rentals

1. Stone Circle Glamping

2. Peartree Serviced Apartments

3. Charles Hope Salisbury Centre

4. The Coach House Apartment — Stylish Loft Retreat for up to 4 ppl.

5. The Old Stables — Wiltshire Countryside Cottage for up to 6 ppl.

6. The Carriage House — Wiltshire Countryside Cottage for up to 6 ppl.

7. The Summer House — Unique Hilltop Retreat for up to 4 ppl.

8. Cozy & Self Contained The Garden Annex 306

9. Settle Winchester

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

11. The Bike Shed

12. Beautiful New Forest Hideaway

13. Second Nature Southampton

14. 1 bedroom accommodation in Burgate, near Fordingbridge

15. Beautiful, traditional rural cottage

16. Ocean Quay Luxury - Stylish 2 Bed - Has Parking

17. Coventry Road Apartments Flat 1

18. New Forest National Park Studio @Forest Palms

19. Annie’s House in Amesbury

20. 2-Bed House Sleeps 4 - Enclosed Garden - Tv & WiFi

Find vacation rentals that suit your style

Top Winterslow Hotel Reviews

ibis Southampton Centre

The Elizabeth House Hotel

Leonardo Hotel Southampton

voco Southampton by IHG

Hilton Southampton - Utilita Bowl

Norton Park Hotel, Spa & Manor House

DoubleTree by Hilton Southampton

Forest Park Country Hotel & Inn, Brockenhurst, New Forest

Moxy Southampton

Find out more about Winterslow

Frequently asked questions

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