Vacation rentals in Winson

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Top-rated vacation rentals in Winson

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Guest favourite

Condo in Bibury

4.84 out of 5 average rating, 170 reviews

Cosy Cotswolds Cottage, Bibury

Double bed flat, open plan living room kitchen. Suit a couple or two friends. Can accommodate children. The lounge sofa converts to a double bed. On site parking for one car. Ramp to front door, premises on one level, easy access for mobility impaired. Great for walking and sightseeing. Easy driving distance from Bourton, Stow, Cheltenham and Cirencester. Tranquil location, close to village centre. This is a no smoking home. 1.75 miles from Cripps Barn and a third of a mile from the Swan Hotel.

Nov. 28 – Dec. 5

$199 CAD per night

Guest favourite

Cottage in Stratton

4.97 out of 5 average rating, 463 reviews

Short walk to Cirencester; Cotswolds, walks, pubs

Luxury, boutique accommodation for two, our lovingly restored Victorian stable is fully equipped and stylishly decorated with a Scandi meets Provence feel. Escape here to relax or to explore the historic, scenic and culinary delights of the Cotswolds. It's a short walk to Cirencester with its Roman museum, market, shops, cafes and restaurants, or short drive to Cheltenham with its famous Race Course, Music and Literary Festivals. Historic sites, charming villages, walks and cosy pubs await you

Feb. 18 – 25

$223 CAD per night

Guest favourite

Guest suite in Ampney Crucis

5.0 out of 5 average rating, 270 reviews

The Tallet, Self-Contained Country Annex

The Tallet is perfect for couples, nestled away within the quiet village of Ampney Crucis on the outskirts of Cirencester, a busy little market town at the heart of the Cotswolds. The detached annex is on 2 separate levels, self-contained allowing peace/privacy throughout the stay. Accessed down a shared drive to the end of our cottage garden, benefiting from stunning views of the surrounding countryside. Within walking distance to the Crown at Ampney Brook where you can enjoy drinks/food.

Jul. 29 – Aug. 5

$182 CAD per night

Superhost

Guesthouse in Bibury

4.83 out of 5 average rating, 354 reviews

The Small House with a Big Welcome

The Small House, is a quaint detached cottage situated just outside the beautiful Cotswold Village of Bibury. Its a short walk to the typically Cotswold charming village of Bibury and just a short drive from Cirencester, and an 8 minute walk away from Arlington Row, owned by the National Trust, which is one of England’s most iconic and photographed sites, it even appears on the inside cover of UK passports! Use the small house as a base to explore and enjoy a true Cotswold experience.

Oct. 31 – Nov. 7

$173 CAD per night

Guest favourite

Loft in Chedworth, Cheltenham

4.92 out of 5 average rating, 302 reviews

Shrove, rural idyll with breakfast hamper

Relax and soak in the peace and quiet at Shrove Cottage, an idyllic little gem of a property which is self-contained with its own private entrance, roomy modern bathroom with underfloor heating, fully equipped kitchen and bedroom/sitting room area with beautiful views up the Chedworth Valley. A perfect central location for work, rest and play. Breakfast with home-made bread included for you to prepare and eat at your leisure. Available at Shrove Cottage, Pancake Hill. (URL HIDDEN)

Oct. 19 – 26

$157 CAD per night

Guest favourite

Home in Coln Rogers

4.96 out of 5 average rating, 344 reviews

The ultimate luxury hideaway.

The Priest House is situated in the garden of our home on the edge of the village, next to the beautiful Saxon Church of St Andrews. We are only 1.5 miles from the popular wedding venue of Cripps Barn. The cottage sleeps 2 people in one bedroom. It is ideal for a romantic getaway or just a well earned rest! The accommodation in under the tiled roof, the thatched end is a home office. The garden is for your use only, but we will occasionally need to walk through to get to the office.

Oct. 31 – Nov. 7

$314 CAD per night

Guest favourite

Cottage in Chedworth

4.99 out of 5 average rating, 114 reviews

Lavender Cottage - Cosy 2-bedroom Cotswold cottage

Escape the stresses of life in this cosy Cotswolds cottage. Whether you need a winter break with frosty walks, a soak in a warm bath and a good film in front of the fire or a summer getaway with BBQs and country pub gardens, this cottage has what you need. Nestled in the picturesque village of Chedworth, in the centre of the Cotswolds, this cottage is the perfect base from which to explore the beautiful countryside and incredible pubs and restaurants the area has to offer.

Apr. 14 – 21

$305 CAD per night

Guest favourite

Barn in Gloucestershire

4.98 out of 5 average rating, 260 reviews

Luxury medieval barn in Cotswold town centre

Unique barn conversion nestled in a medieval alley in the heart of Fairford - open plan barn living with a snug living room and luxury bathroom. Climb the spiral staircase to the boutique bedroom or relax in the pretty, enclosed stone walled garden. We're next door to a lovely 15th century inn with a choice of other pubs nearby; Italian restaurant; local shops; pharmacy; cafes and takeaways on hand - a perfect base to explore this lovely part of the world!

Apr. 1 – 8

$258 CAD per night

Guest favourite

Guesthouse in Withington

4.99 out of 5 average rating, 257 reviews

Stylish studio apartment with breakfast hamper.

Nestled in the Cotswold countryside, Pillars Loft offers a hideaway perfect for two, with stylish interiors, modern amenities and luxurious home comforts. Bordering the regency spa town of Cheltenham and the charming market town of Cirencester, Pillars is perfectly located for those looking to enjoy a spot of retail therapy, fine dining or festival scene that Cheltenham is renowned for while also catering for those looking for a peaceful rural retreat.

Jan. 22 – 29

$178 CAD per night

Guest favourite

Cottage in Northleach

4.91 out of 5 average rating, 177 reviews

Peace and natural beauty in the heart of Cotswolds

Set in the heart of the Cotswolds this charming cottage is perfect for a exploring the many delights the area has to offer! The cottage itself is set back from the road and has use of a large garden and orchard as well as its own private outdoor eating area. The cottage is both spacious, with plenty of space for games and socialising, yet cosy with a wood burner for snug winter nights. It's ideal for either a family or a group of friends.

Oct. 12 – 19

$213 CAD per night

Superhost

Cottage in Chedworth

4.86 out of 5 average rating, 257 reviews

Littlecote Cottage, Cotswolds

Littlecote Cottage is a charming two bedroom, one bathroom cottage, nestled in the picturesque village of Chedworth in the heart of the Cotswolds. Littlecote is tastefully decorated featuring traditional oak beams, exposed brickwork, flagstone floors as well as all modern conveniences. The sitting room features an original inglenook fireplace with wood burning stove (logs provided) and a window seat overlooking Chedworth Valley.

Jul. 10 – 17

$178 CAD per night

Guest favourite

Guesthouse in Cheltenham

4.98 out of 5 average rating, 113 reviews

Leighterton, a beautiful Cotswold hideaway

Leighterton is a new bolthole in the heart of the Cotswold. The small, but perfectly formed, annex offers a beautifully designed, well-equipped space to stay. Surrounded by fields guests can enjoy walks, cycling and exploring neighboring villages. We are also perfectly located for guests of weddings at Cripps and Stone Barn. Located in a separate building next to the main house you have both security and privacy.

Sep. 8 – 15

$209 CAD per night