Plan your trip

A historic building with large windows and pointed arches, surrounded by lush green trees and a grassy area with people sitting and walking.

Search Winchester Cottage Rentals from CA $202

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

    Sign in

  • Be picky

    Search almost a million properties worldwide

    • Find vacation rentals that suit your style

    Cabins

    Apartments

    Cottages

    Aparthotels

    Chalets

    Villas

    Condos

    Houseboats

    Check prices for these dates

    Check prices for these dates, December 13–14, 2026

    View in a map

    Our top choices for Winchester cottages

    1. Suetts Farm Barns

    A modern building with a sloped roof, large windows, and a wooden fence in front.

    2. The Box - Oasis Farm

    A teal RV with a wooden staircase leading to a deck area, a small indoor space with a chair, and a blue patterned mat on the ground.

    3. 3 bedroom accommodation in Andover

    A narrow alleyway with brick buildings, a white door, and a wooden fence.

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

    A two-story house with a front porch, a small garden with various plants and flowers, and a visible chimney.

    5. Boutique Gathering House

    A single-story house with a brick facade, a small porch, and a mailbox indicating the address.

    6. Elm Tree House - UK51762

    A brick house with a sloped roof, a small patio with outdoor furniture, and a gravel ground.

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

    A wooden building with a brick facade, large windows, and a door with a wreath.

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

    A wooden house with a sloped roof, a glass door entrance, and a patio area with outdoor furniture.

    9. 1 bedroom accommodation in Burgate, near Fordingbridge

    A traditional thatched-roof cottage with a brick extension, a white door, and a small window.

    10. Maplescombe - a 3 bedroom cottage in Newton Valence near Alton

    A modern living room with a flat-screen TV, a wooden coffee table with fruit, a grey sofa, and a dining area with a table and chairs.

    11. Barley Cottage

    A black building with a gravel driveway, a door, and a window.

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

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

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

    A log cabin with a large lawn, a dining area with a table and chairs, and a covered patio.

    14. Charming thatched countryside hideaway with beams and garden access

    A thatched-roof cottage with brick walls, a white door, and a gravel driveway.

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

    A two-story house with a brick facade, a tiled driveway, and a wooden gate.

    16. 2 bedroom accommodation in Bramley, near Tadley

    A two-story building with a brick facade and a gravel driveway.

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

    A balcony with a table and chairs, a wooden fence, and a view of a golf course.

    18. The Old Abbey Farmhouse

    A stone manor with a prominent tower, surrounded by a well-maintained lawn and a wooden fence.

    19. The Cheese House

    A traditional brick house with a garden in front, featuring a pathway and a metal fence.

    20. “A charming retreat with a story to tell”

    A black door with a brass plate, a window, and a small brass knocker.

    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.

    View all properties

    Learn more about Winchester

    Medieval majesty awaits at Winchester Cathedral, where centuries of royal history unfold beneath Europe's longest Gothic nave. Explore Jane Austen's final home, then time your visit for the magical Christmas Market or discover distant galaxies at the Science Centre and Planetarium.

    See all hotels in Winchester

    A historic building with large windows and pointed arches, surrounded by lush green trees and a grassy area with people sitting and walking.

    Frequently Asked Questions

    How much do cottages in Winchester cost?

    Rates for cottages in Winchester range between CA $202 and CA $2,548 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 9.2. 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 travellers 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 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.

    Explore a world of travel with Expedia