Vacation rentals in Winchcombe

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Top-rated vacation rentals in Winchcombe

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Cottage in Cheltenham

4.9 out of 5 average rating, 411 reviews

The Bothy cottage in the Cotswolds

The Bothy is a conversion of a 17th Century Cotswold stone stable and a 20th Century kennel building. On the ground floor is the living room with a beautiful wood burning stove, a fully equipped kitchen, a comfortable double bedroom and a modern shower room. Whilst upstairs, which is accessed from a narrow oak staircase, you can find the twin bedroom. The living room has been fitted to retain all its original features and is furnished in period style. I have included many Georgian and Victorian pieces and have also included a large settee and two arm chairs, dining table and chairs for 4, corner cupboard and a dash of the 21st Century with a Sky television. The Bothy is beautifully situated in the Postlip Coombe on the leeward side of the Cotswolds highest hill and yet only minutes from Winchcombe, a classic Cotswold "wool" town, renowned for its excellent shops, restaurants and architecture.

Nov 3 – 10

G$26,552 GYD per night
Guest favorite

Guest suite in Winchcombe

4.94 out of 5 average rating, 116 reviews

The Annex Self contained suite on a working farm

A self-contained annex on a working farm in the beautiful Cotswold town of Winchcombe. Sitting above the medieval town, the room has spectacular views of the surrounding cotswold hills. Situated 10 minutes walk from the centre of town with lots of pubs, shops and restaurants. Right on the Winchcombe Way and close to the Cotswold Way its ideal for walkers. Secure cycle storage is also available. Broadway, Stow-on-the Wold, Bourton-on-the -Water Cheltenham, Stratford and Oxford are all drivable

Jul 31 – Aug 7

G$20,871 GYD per night
Guest favorite

Cottage in Winchcombe

4.84 out of 5 average rating, 154 reviews

Penny Cottage - Cosy Cotswold cottage

Penny Cottage is in the heart of the former Saxon town of Winchcombe. It is a traditional Cotswold cottage with a working inglenook fireplace. It is on the Cotswold Way and has access to miles of country walks. Sudeley Castle, the resting place of the only Queen of England to be buried outside a royal palace, is within walking distance. A variety of pubs and restaurants can all be found within a 5 minute walk. The town also boasts a variety of independent shops, and two small supermarkets.

Apr 24 – May 1

G$26,171 GYD per night

Popular amenities for Winchcombe vacation rentals

Stay near Winchcombe's top sights

Sudeley Castle248 locals recommend
The Royal Oak76 locals recommend
Belas Knap Long Barrow37 locals recommend
GWSR Winchcombe Station19 locals recommend
White Hart Inn28 locals recommend
Hailes Abbey40 locals recommend

Other great vacation rentals in Winchcombe

Guest favorite

Home in Winchcombe

5.0 out of 5 average rating, 82 reviews

'Fifteen off the Green'- 1 Bedroom Cotswolds Home

Oct 5 – 12

G$27,772 GYD per night
Guest favorite

Cottage in Winchcombe

4.93 out of 5 average rating, 95 reviews

The Feathered Nest- idyllic Cotswolds escape.

Feb 20 – 27

G$27,764 GYD per night
Guest favorite

Home in Winchcombe

4.89 out of 5 average rating, 83 reviews

Boutique cottage in the heart of Winchcombe

Apr 23 – 30

G$26,189 GYD per night
Guest favorite

Home in Winchcombe

4.97 out of 5 average rating, 33 reviews

Cosy Cotswold Cottage near Cheltenham

Jun 14 – 21

G$33,230 GYD per night
Guest favorite

Home in Winchcombe

4.9 out of 5 average rating, 20 reviews

Nikolaus Cottage Cotswolds

Dec 5 – 12

G$40,973 GYD per night
Guest favorite

Home in Winchcombe

4.93 out of 5 average rating, 54 reviews

Beam House, Winchcombe, sleeps 6 + 2

Feb 19 – 26

G$74,379 GYD per night
Guest favorite

Home in Winchcombe

4.95 out of 5 average rating, 96 reviews

Anchor Weighbridge House Winchcombe - 4 bedroom

Aug 16 – 23

G$110,115 GYD per night
Guest favorite

Cottage in Winchcombe

4.94 out of 5 average rating, 50 reviews

Thimble Cottage. Winchcombe

Dec 5 – 12

G$41,905 GYD per night
Guest favorite

Cottage in Winchcombe

4.93 out of 5 average rating, 58 reviews

Cosy Cotswold Cottage in the centre of Winchcombe

Feb 2 – 9

G$42,996 GYD per night
Guest favorite

Home in Winchcombe

4.96 out of 5 average rating, 53 reviews

Barebones Farm, Winchcombe, Cotswolds

Feb 3 – 10

G$152,446 GYD per night
Guest favorite

Home in Winchcombe

4.92 out of 5 average rating, 39 reviews

Town Centre cottage with garden & parking

Jun 16 – 23

G$42,765 GYD per night
Guest favorite

Cottage in Winchcombe

5.0 out of 5 average rating, 13 reviews

Stunning 2 Bed Cotswold Cottage Winchcombe

Feb 25 – Mar 4

G$58,417 GYD per night

Quick stats about vacation rentals in Winchcombe

Total rentals

130 properties

Rentals with dedicated workspaces

30 properties have a dedicated workspace

Pet-friendly rentals

60 properties allow pets

Family-friendly rentals

90 properties are a good fit for families

Total number of reviews

8.5K reviews

Nightly prices starting at

G$14,661 GYD before taxes and fees

Frequently Asked Questions

  • Where should I stay in Winchcombe?

    Make yourself at home in Winchcombe by choosing from our most frequently booked neighborhoods. We have over 200 vacation rentals in Gretton, over 240 vacation rentals in Winchcombe, and over 200 vacation rentals in Greet.

  • Do house rentals in Winchcombe have a kitchen?

    Absolutely! We offer over 30 house rentals with a kitchen in Winchcombe. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Winchcombe?

    Four-legged friends are welcome in Winchcombe. Choose from more than 60 vacation rentals for guests traveling with pets.

  • Do cottage rentals in Winchcombe have wifi?

    Absolutely! We offer over 60 cottage rentals with wifi in Winchcombe. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in cottage rentals in Winchcombe?

    Experience the best of Winchcombe with our cottage rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly vacation rentals in Winchcombe?

    Winchcombe has more than 90 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for House Rentals in Winchcombe?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with free parking, over 30 homes with a kitchen, over 40 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there vacation rentals with a dedicated workspace in Winchcombe?

    Yes! Work meets play with ease at over 30 vacation rentals in Winchcombe featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

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