A large red brick building with a central entrance flanked by columns, a fountain in front, and trees on either side.

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Winchester cottages

A white, two-story building with a curved corner, a brick base, and a small balcony on the second floor.

1. Clifton Lodge

Clifton Lodge
2.0 star property
Winchester
$639 nightly
The price is $766
Oct 7 - Oct 8
Total with taxes and fees
Clifton Lodge
A riverside walkway with a brick wall, benches, and potted plants.

2. Rivergem - Riverside Coach House

Rivergem - Riverside Coach House
2.0 star property
Winchester City Center
$953 nightly
The price is $1,144
Oct 7 - Oct 8
Total with taxes and fees
Rivergem - Riverside Coach House
A black building with a gravel driveway, a door, and a window.

3. Barley Cottage

Barley Cottage
3.0 star property
Alresford
$893 nightly
The price is $1,071
Oct 7 - Oct 8
Total with taxes and fees
Barley Cottage
A small brick house with a dark roof and a chimney, surrounded by a gravel driveway and greenery.

4. 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
9.6 out of 10, Exceptional, (15 reviews)
"Fabulous place to stay."
United States
CHRISTOPHER S.
$602 nightly
The price is $602
Oct 4 - Oct 5
Total with taxes and fees
The Stables, Wickham - a barn conversion that sleeps 2 guests in 1 bedroom
A wooden table with two chairs and a glass of water, overlooking a body of water with boats.

5. Watersedge Cabin - Luxury Cottages

Watersedge Cabin - Luxury Cottages
Sarisbury Green
$578 nightly
The price is $578
Oct 4 - Oct 5
Total with taxes and fees
Watersedge Cabin - Luxury Cottages
A single-story brick building with a tiled roof, a car parked in front, and a gravel driveway.

6. A family friendly or couples base to explore the local sights and attractions.

A family friendly or couples base to explore the local sights and attractions.
Hamble
10.0 out of 10, Exceptional, (1 review)
"Very homely and comfortable with all the needs to make it a pleasant and lovely stay. The location very good for access to motorway and other routes to places of interest. As we are familiar with area it was ideal for visiting family and friends .Very Good"
United Kingdom
Stella C.
$671 nightly
The price is $671
Oct 7 - Oct 8
Total with taxes and fees
A family friendly or couples base to explore the local sights and attractions.
A row of wooden cabins with attached porches, each with a small porch light.

7. 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, (17 reviews)
"Lovely accommadition all you could need for a get away, we only stayed 1 night wish it could have been more. Only issue main entrance is rather secluded.Hope to return for a longer stay, peaceful and secluded"
United States
Diana T.
$207 nightly
The price is $207
Oct 8 - Oct 9
Total with taxes and fees
Farm Cottage on a Secluded 9-acre Equestrian Small Holding
A two-story house with a front porch, a small garden with various plants and flowers, and a visible chimney.

8. Cliffside Cosy Cottage by Cowes Beach: 1x KING-Size Double BR & a Twin/Kids BR

Cliffside Cosy Cottage by Cowes Beach: 1x KING-Size Double BR & a Twin/Kids BR
Cowes
10.0 out of 10, Exceptional, (26 reviews)
"Awesome place to stay- we absolutely loved it and will be back"
United Kingdom
Edward
$185 nightly
The price is $185
Oct 7 - Oct 8
Total with taxes and fees
Cliffside Cosy Cottage by Cowes Beach: 1x KING-Size Double BR & a Twin/Kids BR
A narrow alleyway with brick buildings, a white door, and a wooden fence.

9. 3 bedroom accommodation in Andover

3 bedroom accommodation in Andover
Andover
$1,231 nightly
The price is $1,231
Oct 11 - Oct 12
Total with taxes and fees
3 bedroom accommodation in Andover
Exterior

10. Moonwood House - Welcome to country living at its very finest.

Moonwood House - Welcome to country living at its very finest.
Beaulieu
9.8 out of 10, Exceptional, (11 reviews)
"Superb accommodation pristine throughout, ideal location for local pubs walks and restaurants, Would recommend for a family get together, the children loved it too"
United States
Anonymous traveler
$3,301 nightly
The price is $3,301
Oct 7 - Oct 8
Total with taxes and fees
Moonwood House - Welcome to country living at its very finest.
A traditional thatched-roof house with a brick facade, a white door, and a window.

11. 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)
"Great location. Close to hiking and cycling trails in New Forest. Nice pubs nearby (need to drive). Quaint cottage which is well equipped for a small family (we had 2 adults and 2 kids under 16). Parking on prem and a nice little garden outside."
United States
Rahul Naithani
$258 nightly
The price is $258
Oct 8 - Oct 9
Total with taxes and fees
1 bedroom accommodation in Burgate, near Fordingbridge
A log cabin with a large lawn, a dining area with a table and chairs, and a covered patio.

12. Taylors Copse Cottage by inspirestays.com - a cottage that sleeps 5 guests in 2 bedrooms

Taylors Copse Cottage by inspirestays.com - a cottage that sleeps 5 guests in 2 bedrooms
Steep Marsh
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful holiday cottage, wonderful surroundings, lovely hosts. We have had a wonderful holiday."
Germany
S v.
$796 nightly
The price is $796
Oct 7 - Oct 8
Total with taxes and fees
Taylors Copse Cottage by inspirestays.com - a cottage that sleeps 5 guests in 2 bedrooms
A white house with a brick roof, a garden with a swimming pool, and a patio area with outdoor furniture.

13. Coppice Hill House

Coppice Hill House
3.0 star property
Southampton
$1,379 nightly
The price is $1,655
Oct 15 - Oct 16
Total with taxes and fees
Coppice Hill House
A cabin with a wooden door, a porch with benches, and a sign indicating it's a cabin.

14. Taylors Copse Cabin by inspirestays-com - a cottage that sleeps 2 guests in 1 bedroom

Taylors Copse Cabin by inspirestays-com - a cottage that sleeps 2 guests in 1 bedroom
Steep Marsh, nr Petersfield
10.0 out of 10, Exceptional, (1 review)
"I'm very local but needed different surroundings to relax and recharge and thanks to this lovely cabin, hosts and location I achieved this. Would highly recommend and would visit again. The cabin exceeded expectations and is very peaceful and tranquil with woodland surrounds. I had everything I needed and the hosts went above and beyond. The whole experience, cabin, furnishings and location was perfect just the way it was, I wouldn't change anything other than staying longer. Beautiful!"
United States
Anonymous traveler
$712 nightly
The price is $712
Oct 7 - Oct 8
Total with taxes and fees
Taylors Copse Cabin by inspirestays-com - a cottage that sleeps 2 guests in 1 bedroom
A two-story house with a brick facade, a tiled driveway, and a wooden gate.

15. Grove Lodge - a house that sleeps 13 guests in 5 bedrooms

Grove Lodge - a house that sleeps 13 guests in 5 bedrooms
Gosport
9.6 out of 10, Exceptional, (18 reviews)
"The house and gardens were perfect for our family gathering."
United Kingdom
Jessica J.
$1,339 nightly
The price is $1,339
Oct 7 - Oct 8
Total with taxes and fees
Grove Lodge - a house that sleeps 13 guests in 5 bedrooms
An outdoor patio with a wooden table, two chairs, a large umbrella, and a bottle of wine.

16. The Dairy at Copper Beeches

The Dairy at Copper Beeches
Petersfield
$548 nightly
The price is $548
Oct 30 - Oct 31
Total with taxes and fees
The Dairy at Copper Beeches
Terrace/patio

17. Squirrel Haven - Woodland Retreat

Squirrel Haven - Woodland Retreat
Wootton Bridge
10.0 out of 10, Exceptional, (6 reviews)
"Excellent stay with very friendly and helpful host. the property was spotlessly clean and really well equipped with the bonus of the occasional red squirrel in the garden."
United States
Anonymous traveler
$835 nightly
The price is $835
Oct 7 - Oct 8
Total with taxes and fees
Squirrel Haven - Woodland Retreat
A residential area with houses, a well-maintained lawn, and a clear sky.

18. Beacon Square, Emsworth - a family house that sleeps 8 guests in 3 bedrooms

Beacon Square, Emsworth - a family house that sleeps 8 guests in 3 bedrooms
Emsworth
8.0 out of 10, Very good, (17 reviews)
"Great stay had by my husband, 2 teenagers and me "
United Kingdom
Paulette M.
$1,077 nightly
The price is $1,077
Oct 7 - Oct 8
Total with taxes and fees
Beacon Square, Emsworth - a family house that sleeps 8 guests in 3 bedrooms
A balcony with a table and chairs, a wooden fence, and a view of a golf course.

19. Stunning property and location with fabulous views overlooking Wootton Creek.

Stunning property and location with fabulous views overlooking Wootton Creek.
Wootton Bridge
10.0 out of 10, Exceptional, (4 reviews)
"very comfortable and cozy cottage, well equipped and fabulous view"
United Kingdom
Rosalind M.
$307 nightly
The price is $307
Oct 30 - Oct 31
Total with taxes and fees
Stunning property and location with fabulous views overlooking Wootton Creek.
A stone manor with a prominent tower, surrounded by a well-maintained lawn and a wooden fence.

20. The Old Abbey Farmhouse

The Old Abbey Farmhouse
Ryde
10.0 out of 10, Exceptional, (28 reviews)
"Everything, the cleanliness, the facilities, the location, the thoughtfulness of the essentials provided"
United States
Gavin
$984 nightly
The price is $984
Oct 11 - Oct 12
Total with taxes and fees
The Old Abbey Farmhouse
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 Winchester Hotel Reviews

Leonardo Hotel Southampton

Leonardo Hotel Southampton

8/10 Good
"Nice place and will stay again"
Michael 1-night trip
Posted 18 hours ago
Leonardo Hotel Southampton

Find out more about Winchester

Winchester Cottages information

Number of reviews
177
Accommodation
742 Cottages
Lowest Price
$185
Highest Price
$3,301

Frequently asked questions

How much do cottages in Winchester cost?
Rates for cottages in Winchester range between $185 and $3,301 per night. No matter your budget, you're sure to find an ideal place to get in touch with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best cottages in Winchester?
Take your pick of multiple cottages in Winchester with a total average guest review rating of 9.7. Hang Your Hat - The Cottage is a fantastic place to rest and put your feet up between adventures. This 4-star cottage also features a garden and a barbecue grill. Cardew House Cottage is another top pick with travelers to this area. It has a 3.5-star rating and amenities including a deep soaking bathtub and individually decorated rooms.
How many cottages are there in Winchester?
Get in touch with nature in one of the 742 cottages located in Winchester. To help you select a property that's right for you, use our filters to search for perks or amenities you prefer.
Are there any family-friendly cottages in Winchester?
Spend your family vacay at Hang Your Hat - The Cottage, a 4-star cottage just a short drive from town. Amenities here include a barbecue grill and WiFi. Another family-friendly option where you can swap the urban jungle for wide open spaces is Cardew House Cottage. An oven and WiFi help make this 3.5-star cottage a hit with guests. Winchester boasts loads of family-friendly attractions to check out that'll keep the kids entertained. Marwell Zoo and Winchester Science Centre and Planetarium promise a fun day out for everyone.
Why book your cottage in Winchester with Expedia?
Expedia has some terrific cottages in Winchester, so start planning for a memorable stay close to nature. If you're sticking to a budget, choose how much you're willing to spend and your preferred property star rating. Or, use our handy filters to search for cottages with a pool or a hot tub. We'll help you find the right fit whatever your trip looks like.
How can I find cheap cottages in Winchester?
A wonderful way to get cheap cottages in Winchester is with Expedia's user-friendly filter tool. Narrow down your search results by star rating, budget and amenities to discover unbeatable prices in just a few clicks.
What is there to do in Winchester near my cottage?
Winchester has enough experiences to keep you on the go for weeks (or months!), starting with Queen Eleanors Garden. Royal Green Jackets Museum, Wolvesey Castle and Marwell Zoo are other well-known attractions. If you're lingering longer, Great Hall and King Alfred the Great Statue will add the finishing touches to your itinerary.

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