Photo by C J West

Search Cottages in Winchester

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Our top choices for Winchester cottages

Squirrel's Leap

Squirrel's Leap
3.0 star property
Winchester
The price is AED 1,963
AED 2,356 total
includes taxes & fees
27 Dec - 28 Dec
Squirrel's Leap

Peaceful Elevated Residential Area - Walk to City

Peaceful Elevated Residential Area - Walk to City
5.0 star property
Winchester
The price is AED 1,306
AED 1,568 total
includes taxes & fees
31 Dec - 1 January 2026
Peaceful Elevated Residential Area - Walk to City

Rivergem - Riverside Coach House

Rivergem - Riverside Coach House
2.0 star property
Winchester
The price is AED 2,306
AED 2,767 total
includes taxes & fees
29 Dec - 30 Dec
Rivergem - Riverside Coach House

Stonehenge Cottages

Stonehenge Cottages
5.0 star property
Salisbury
9.8 out of 10, Exceptional, (105)
"Information, including a video, provided by the friendly owners before and during our stay was excellent. The beautifully appointed cottage was convenient for Salisbury and for the nearby pub which serves good food. We will definitely stay there again, if in the area."
United Kingdom
Fiona
The price is AED 774
AED 929 total
includes taxes & fees
4 Jan - 5 January 2026
Stonehenge Cottages

Groomes Country House

Groomes Country House
3.5 star property
Bordon
The price is AED 12,356
AED 14,827 total
includes taxes & fees
29 Dec - 30 Dec
Groomes Country House

Century House - a house that sleeps up to 8 guests in 4 bedrooms

Century House - a house that sleeps up to 8 guests in 4 bedrooms
Gosport
9.2 out of 10, Wonderful, (7)
"The house suited our family group of 8 really well. The house was clean and tidy with a well equipped kitchen. Although we had a couple of mishaps during our stay the property manager dealt with them efficiently and politely. We would stay in this property again. "
United Kingdom
Tim Y.
The price is AED 8,994
AED 8,994 total
includes taxes & fees
31 Dec - 1 January 2026
Century House - a house that sleeps up to 8 guests in 4 bedrooms

Bell Cottage

Bell Cottage
Cowes
10.0 out of 10, Exceptional, (8)
"Anonymous: Accommodation lovely. Owners seem to have thought of everything to make our stay very pleasant. Nicely situated to explore the Island. Enjoyed our stay."
United States
Anonymous traveler
The price is AED 15,726
AED 17,519 total
includes taxes & fees
15 Jan - 16 January 2026
Bell Cottage

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)
"Lovely 1 night stay in beautiful location. Louise very welcoming and property was perfect and very clean."
United Kingdom
Emily S.
The price is AED 818
AED 931 total
includes taxes & fees
21 Dec - 22 Dec
Farm Cottage on a Secluded 9-acre Equestrian Small Holding

Flowering - Ashling Park - sleeps 4 guests in 2 bedrooms

Flowering - Ashling Park - sleeps 4 guests in 2 bedrooms
Chichester
The price is AED 2,773
AED 2,773 total
includes taxes & fees
21 Dec - 22 Dec
Flowering - Ashling Park - sleeps 4 guests in 2 bedrooms

Charming 3 bed Thatched cottage in rural village near Stockbridge Winchester.

Charming 3 bed Thatched cottage in rural village near Stockbridge Winchester.
Stockbridge
9.6 out of 10, Exceptional, (99)
"Charming cottage. "
United States
Debbie
The price is AED 774
AED 877 total
includes taxes & fees
22 Dec - 23 Dec
Charming 3 bed Thatched cottage in rural village near Stockbridge Winchester.

Double Award Winning, Stunning 1700's Grade 2 listed cottage near Stonehenge

Double Award Winning, Stunning 1700's Grade 2 listed cottage near Stonehenge
Salisbury
10.0 out of 10, Exceptional, (5)
"This was a perfect place for our family of five. Hosts were friendly and communicative. Loved the proximity to Stonehenge and Salisbury Cathedral (short car ride to both). We would definitely stay again."
United States
Rebecca
The price is AED 836
AED 949 total
includes taxes & fees
22 Dec - 23 Dec
Double Award Winning, Stunning 1700's Grade 2 listed cottage near Stonehenge

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, (3)
"very comfortable and cozy cottage, well equipped and fabulous view"
United Kingdom
Rosalind M.
The price is AED 1,032
AED 1,032 total
includes taxes & fees
3 Jan - 4 January 2026
Stunning property and location with fabulous views overlooking Wootton Creek.

Charming thatched countryside hideaway with beams and garden access

Charming thatched countryside hideaway with beams and garden access
2.0 star property
Fordingbridge
The price is AED 1,022
AED 1,268 total
includes taxes & fees
31 Dec - 1 January 2026
Charming thatched countryside hideaway with beams and garden access

Meadow Cottage

Meadow Cottage
4.0 star property
Salisbury
10.0 out of 10, Exceptional, (4)
"Perfect for our needs, well furnished, comfortable and lovely walk across the water meadows into town (approx 15-20 mins)"
United Kingdom
Colin
The price is AED 734
AED 881 total
includes taxes & fees
5 Jan - 6 January 2026
Meadow Cottage

Aquanaut

Aquanaut
3.5 star property
Cowes
The price is AED 13,221
AED 15,865 total
includes taxes & fees
27 Dec - 28 Dec
Aquanaut

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)
"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.
The price is AED 1,302
AED 1,302 total
includes taxes & fees
8 Jan - 9 January 2026
A family friendly or couples base to explore the local sights and attractions.

The Box - Oasis Farm

The Box - Oasis Farm
Fareham
The price is AED 929
AED 929 total
includes taxes & fees
4 Jan - 5 January 2026
The Box - Oasis Farm

A spacious and well presented bungalow with amazing views over Berkshire.

A spacious and well presented bungalow with amazing views over Berkshire.
Reading
10.0 out of 10, Exceptional, (1)
"Great location and beautiful garden with views across the hills. Spotlessly clean and well maintained with all the things you may need for your holiday. The caretakers were very friendly and helpful and cared about us and the property with pride. Local supermarkets, petrol station and IKEA were only a mile down the road plus a five minute walk from the property was a pub serving food and an excellent fish n chips shop! Buses into town from outside the chippy were every 10 minutes or sooner!"
United States
Michael Jeffs
The price is AED 2,295
AED 2,295 total
includes taxes & fees
2 Jan - 3 January 2026
A spacious and well presented bungalow with amazing views over Berkshire.

The Old Abbey Farmhouse

The Old Abbey Farmhouse
Ryde
10.0 out of 10, Exceptional, (26)
"Everything, the cleanliness, the facilities, the location, the thoughtfulness of the essentials provided"
United States
Gavin
The price is AED 3,177
AED 3,765 total
includes taxes & fees
9 Jan - 10 January 2026
The Old Abbey Farmhouse

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, (9)
"Beautiful holiday cottage, wonderful surroundings, lovely hosts. We have had a wonderful holiday."
Germany
S v.
The price is AED 2,854
AED 2,854 total
includes taxes & fees
6 Jan - 7 January 2026
Taylors Copse Cottage by inspirestays.com - a cottage that sleeps 5 guests in 2 bedrooms
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

Top Winchester Hotel Reviews

Frequently asked questions

How much do cottages in Winchester cost?
Rates for cottages in Winchester range between AED 877 and AED 17,519 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 9.8. 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 653 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.
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.