Vacation rentals in Winchcombe

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Top-rated vacation rentals in Winchcombe

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Guest favorite

Cottage in Cheltenham

4.9 out of 5 average rating, 417 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.

Sep 3 – 10

R2,380 ZAR per night

Guest favorite

Guest suite in Winchcombe

4.93 out of 5 average rating, 120 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

Oct 6 – 13

R1,919 ZAR per night

Guest favorite

Shepherd’s hut in Winchcombe

4.96 out of 5 average rating, 439 reviews

Idyllic, Cotswold Views, En suite, TV/Wi-Fi

Scandinavian styled, ensuite, luxury Shepherd's Hut set in peaceful private countryside. Bright & open aspect with extensive hillside views. Perfectly located in an Area of Outstanding Natural Beauty, The Cotswolds. Local & National Walking Trails on the doorstep. Picturesque 20/25 minute walk or cycle (hire one of our e-bikes!) to medieval Winchcombe; home to the fascinating & majestic Sudeley Castle. You’ll also find many unique, independent shops, excellent restaurants, superb cafés & pubs.

Jul 9 – 16

R2,013 ZAR per night

Guest favorite

Cottage in Winchcombe

4.84 out of 5 average rating, 156 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.

Dec 29 – Jan 5

R3,491 ZAR per night

Superhost

Cottage in Winchcombe

4.8 out of 5 average rating, 105 reviews

Idyllic cottage with direct Access to Cotswold Way

A rare opportunity to stay in a historic cottage. Nestled in an Area of Outstanding Natural Beauty, this 300-year-old and Grade II listed hideaway offers a peaceful, idyllic stay within a 15-minute drive from Cheltenham. It has a private garden with DIRECT ACCESS to the Cotswold Way! Great to cosy up on wet days, and even better to explore the area or enjoy our garden on a sunny day. Perfect for romantic getaways, nature lovers or people who want to escape the humdrum of everyday life.

Sep 5 – 12

R4,834 ZAR per night

Guest favorite

Cottage in Stanley Pontlarge

4.99 out of 5 average rating, 158 reviews

Stunning Cotswold cottage, log burner, Winchcombe

Gorgeous romantic Cotswold cottage with direct access to walks. Up to 2 well behaved dogs welcome. The Old Mill House is a luxury retreat in Stanley Pontlarge, 2 miles to Winchcombe, 5 miles Cheltenham Racecourse, 9 miles central Cheltenham. Living room with TV and logburner, bedroom with kingsize bed, kitchen with microwave, dishwasher, induction hob, oven Nespresso machine, Smeg fridge/freezer. Shower room. Neal's Yard toiletries. Fast broadband. EV charging. Muddy paw pet washer.

Jan 22 – 29

R3,593 ZAR per night

Guest favorite

Guesthouse in Winchcombe

4.96 out of 5 average rating, 292 reviews

Charming ‘mini cottage’ bedroom and shower room

A pretty and private little Cotswold stone bakehouse converted to a bedroom and shower room with beautiful Cotswold views set in rolling farmland on edge of historic hamlet of Hailes. We are right on the Cotswold Way and an ideal stop off after the first leg or walk the myriad of footpaths around us straight from the door. Within easy access of Cheltenham racecourse and the lovely villages of the Cotswolds, the many country pubs or a visit to the amazing Giffords Circus.

Dec 8 – 15

R2,444 ZAR per night

Guest favorite

Guest suite in Broadway

4.99 out of 5 average rating, 147 reviews

Cosy countryside studio with log burner stove

The Studio at Hoo Lodge provides cosy accommodation for two in the tranquil village of Laverton, near Broadway Double French doors to front Exposed beam ceiling & stone end wall Log burner, SMART TV & leather sofa Iron double bed & king-size duvet Kitchen diner area, gas cooker, fridge, kettle & toaster Shower room with dual shower head Linens, towels & logs included. Patio with teak table & chairs Ideal location for exploring, walking, running & biking or just relaxing.

Apr 5 – 12

R2,303 ZAR per night

Guest favorite

Cottage in Winchcombe

4.89 out of 5 average rating, 187 reviews

Luxurious Escape: Charming Dog-Friendly Cottage

Welcome to The Bolt Hole, a unique, Cotswold stone cottage, in the centre of stunning, Winchcombe close to restaurants, cafes and historic Sudeley Castle. - Romantic bedroom & super comfortable Hypnos king-size mattress - 400+ thread-count cotton bed linen - En-suite bathroom: large shower and roll-top bath - Wall-mounted Smart TV - Dog friendly - Romantic log burner - Large refurbished kitchen - Cot available Complimentary late check out of 11am and no cleaning fees

May 29 – Jun 5

R5,319 ZAR per night

Guest favorite

Cottage in Winchcombe

4.92 out of 5 average rating, 227 reviews

No. 15 North Street, Cotswolds cottage

Rustic 200 year old Cotswolds cottage, lovingly restored into the ultimate countryside retreat- pet friendly, huge inglenook fireplace, roll top bath, private courtyard garden and a stones throw from the local pub... No.15 is perfectly positioned in the heart of Winchcombe, surrounded by independent shops and award winning pubs and restaurants. Just a short stroll from Sudeley Castle and the Cotswolds Way, this cosy cottage is the perfect place to escape the every day

Jul 5 – 12

R5,180 ZAR per night

Guest favorite

Cottage in Winchcombe

4.84 out of 5 average rating, 105 reviews

Barley Cottage

A character filled centrally-located cottage sure to enable a relaxing stay in our picturesque Cotswold town. An indoor log burner keeps the place cosy, and a small patio with garden to the rear of the cottage allows for outdoor dining during the summer. Cook for yourselves in the fully equipped kitchen or eat out at the many eateries in town right on the doorstep. A fully refurbished bathroom with walk in shower and sofa bed that can sleep 2 are also at your leisure.

Jul 28 – Aug 4

R2,830 ZAR per night

Guest favorite

Cottage in Winchcombe

4.91 out of 5 average rating, 422 reviews

Cotswold77 - Heart of the Cotswolds

Set in the heart of the Saxon village of Winchcombe a beautifully restored and luxuriously furnished Grade II listed cottage set over three floors with a pretty, sunny garden. Glorious countryside, Cotswold country pubs and a Michelin star restaurant all in walking distance. 6 miles from Cheltenham Racecourse and perfect for the Literature, Jazz and Science Festivals in Cheltenham. An Idyllic spot for exploring the Cotswolds!

Dec 2 – 9

R6,008 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Winchcombe vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Winchcombe's top sights

Sudeley Castle248 locals recommend

Belas Knap Long Barrow37 locals recommend

White Hart Inn28 locals recommend

GWSR Winchcombe Station19 locals recommend

Hailes Abbey40 locals recommend

The Lion Inn41 locals recommend

Other great vacation rentals in Winchcombe

Guest favorite

Guesthouse in Withington

4.99 out of 5 average rating, 257 reviews

Stylish studio apartment with breakfast hamper.

Oct 29 – Nov 5

R2,439 ZAR per night

Guest favorite

Cottage in Winchcombe

4.95 out of 5 average rating, 20 reviews

Cosy 2 Bedroom Cotswold Cottage with Large Garden

Jan 16 – 23

R3,245 ZAR per night

Guest favorite

Cottage in Winchcombe

4.9 out of 5 average rating, 39 reviews

The Vine - a luxurious Cotswold escape for two.

Sep 30 – Oct 7

R2,457 ZAR per night

Guest favorite

Cottage in Winchcombe

5.0 out of 5 average rating, 38 reviews

Little Nook Cottage - Dog Friendly & Large Garden

Mar 30 – Apr 6

R5,011 ZAR per night

Guest favorite

Home in Winchcombe

5.0 out of 5 average rating, 86 reviews

'Fifteen off the Green'- 1 Bedroom Cotswolds Home

Apr 4 – 11

R2,489 ZAR per night

Guest favorite

Home in Winchcombe

4.97 out of 5 average rating, 36 reviews

Cosy Cotswold Cottage near Cheltenham

Oct 8 – 15

R2,979 ZAR per night

Guest favorite

Cottage in Winchcombe

4.92 out of 5 average rating, 63 reviews

Cosy Cotswold Cottage in the centre of Winchcombe

Apr 4 – 11

R3,854 ZAR per night

Guest favorite

Cottage in Winchcombe

4.95 out of 5 average rating, 56 reviews

Thimble Cottage. Winchcombe

Dec 13 – 20

R3,756 ZAR per night

Show all

Quick stats about vacation rentals in Winchcombe

Total rentals
140 properties
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Pet-friendly rentals
70 properties allow pets
Family-friendly rentals
90 properties are a good fit for families
Total number of reviews
8.9K reviews
Nightly prices starting at
R1,343 ZAR 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 210 vacation rentals in Gretton, over 210 vacation rentals in Greet, and over 250 vacation rentals in Winchcombe.
Do house rentals in Winchcombe have a kitchen?
Absolutely! We offer over 40 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 70 vacation rentals for guests traveling with pets.
Do house rentals in Winchcombe have wifi?
Absolutely! We offer over 40 house 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 $70 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 Cottage Rentals in Winchcombe?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 40 homes with free parking, over 60 homes with a kitchen, over 60 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 40 vacation rentals in Winchcombe featuring dedicated workspaces. Stay connected and productive in your home away from home.

Vacation rentals in Winchcombe

Top-rated vacation rentals in Winchcombe

Vacation rentals for every style

Cottages

Houses

Hotels

Popular amenities for Winchcombe vacation rentals

Stay near Winchcombe's top sights

Other great vacation rentals in Winchcombe

Guesthouse in Withington

Cottage in Winchcombe

Cottage in Winchcombe

Cottage in Winchcombe

Home in Winchcombe

Home in Winchcombe

Cottage in Winchcombe

Cottage in Winchcombe

Quick stats about vacation rentals in Winchcombe

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Where should I stay in Winchcombe?

Do house rentals in Winchcombe have a kitchen?

Are there pet-friendly vacation rentals in Winchcombe?

Do house rentals in Winchcombe have wifi?

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

Are there family-friendly vacation rentals in Winchcombe?

What are the most popular amenities for Cottage Rentals in Winchcombe?

Are there vacation rentals with a dedicated workspace in Winchcombe?

Destinations to explore