Cottage holiday rentals in Cheltenham

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Top-rated cottage rentals in Cheltenham

Guests agree: These cottages are highly rated for location, cleanliness and more.

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Top Guest favourite
A charming row of 18th-century cottages is depicted, featuring stone exteriors with traditional slate roofs. Lush vegetation and climbing plants adorn the walls, while windows invite natural light. The pathway, bordered by vibrant flowers, leads to an inviting garden space that enhances the cottage's appeal.
Cottage in Winchcombe
4.93 out of 5 average rating, 153 reviews

The Feathered Nest an idyllic Cotswolds escape.

Nestled in the heart of historic Winchcombe, The Feathered Nest offers a welcoming escape in the beautiful North Cotswolds. Set on picturesque Vineyard Street, this lovingly restored former wool cottage blends timeless character with modern comforts. Thoughtfully renovated by the owners this the boutique two-bedroom home features stylish furnishings and all the contemporary amenities you need for a relaxing stay. Availability from 20th June - five night minimum stay, discount for 7 nights plus.

Superhost
An open plan master bedroom is illuminated by natural light from large windows. A free-standing roll-top bath sits beside the bed, accompanied by a potted plant. Exposed wooden beams add character, while tasteful wall art complements the tranquil decor.
Cottage in Prestbury
4.94 out of 5 average rating, 202 reviews

Luxury Thatched Cotswold Cottage, amazing location

Located in a historic village a stone's throw from Cheltenham's racecourse is our immaculately restored thatched cottage. A choice of 3 pubs, local shop and butcher can be found within walking distance. Ideal for 2 couples sharing or a family with accommodation on 2 floors. Featuring a master suite with roll-top bath and own sitting room which can be converted into a bedroom with a double sofa bed. Downstairs an accessible bedroom with its own separate shower w/c. Full kitchen diner with dog bed

Top Guest favourite
Cottage in Gloucestershire
4.97 out of 5 average rating, 190 reviews

Cottage Nestled within old Cotswold Farmhouse

Take your first glimpse of the rolling fields surrounding our traditional Cotswold stone farmstead, as you travel along our private, tree lined drive. In an AONB, the farmstead sits on the edge of the Golden Valley. Dating back to the 1700s, Little Finch's Cottage is nestled within the original Farmhouse, where you can still find exposed beams and sunny window seats. Step through Little Finch's front door into the lounge/breakfast room which is linked to the bedroom by a steep spiral staircase.

Guest favourite
The exterior of the cottage is framed by climbing ivy and lush greenery, with stone walls reflecting its historic charm. A wooden dining table is set outside, surrounded by well-maintained flower beds, inviting a pleasant outdoor experience.
Cottage in Stanton
4.95 out of 5 average rating, 118 reviews

Stanton Cotswolds The Hay loft 2 Bed, Cottage

Nestled in the centre of the peaceful and picturesque village of Stanton, in the heart of the Cotswolds, you will find the Hayloft. A charming 17th century converted cotswold stone barn. A light and airy cottage with beams and character. Stanton is quintessentially Cotswolds, picture postcard pretty, providing the perfect getaway from the hustle and bustle of everyday life. The Cotswold Way runs through the village which makes it the perfect base if you enjoy walking, cycling and sightseeing.

Top Guest favourite
The living area features a cozy seating arrangement with a neutral-toned sofa and decorative cushions. A natural woven pendant light hangs above, illuminating the space. A rustic coffee table sits on textured flooring, accompanied by warm tones and a charming wreath adorning the entrance.
Cottage in Winchcombe
4.98 out of 5 average rating, 247 reviews

Little Nook Cottage - Cosy & Large Garden

Located in the heart of Winchcombe with far reaching views over the rolling Cotswold hills, Little Nook Cottage is a charming bolt hole, perfect for couples or a small family from which to explore the Cotswolds. You will find beautifully crafted beams and original stone floors paired with all the luxuries you need for a relaxing break. Featuring a cosy living/dining room with wood burning fire, a super comfy double room and even a dedicated work space should you wish to work away from home!

Top Guest favourite
A charming Cotswold stone cottage is depicted, featuring a stone pathway leading to a warm, inviting entrance. Surrounding greenery enhances the rustic ambiance, while the exterior showcases original details and serene landscaping. Bicycles are securely parked nearby, indicating accessibility for outdoor activities.
Cottage in Painswick
5 out of 5 average rating, 204 reviews

Quiet grade 1 listed entire cottage in Cotswolds

A bright and recently modernised grade 1 listed Cotswold stone cottage, 100 yards from the Cotswold Way with breathtaking views down the Stroud Valley, its own parking and secluded outdoor eating. Filled with natural light, it is very peaceful and extremely comfortable with luxury bedding (super king or twin bed) and kitchen. An idyllic spot for walking, cycling, exploring the local scenery or simply escaping the city Painswick is 10 minutes from Stroud ( 87 mins hourly train to London).

Top Guest favourite
Two comfortable chairs are positioned on a patio, overlooking a green paddock with trees and distant hills. A table with a blue drink sits between the chairs, while dogs can be seen playing in the open space under a partly cloudy sky.
Cottage in Bank Farm Barns
4.99 out of 5 average rating, 621 reviews

Charming Dog Friendly Barn Conversion & Paddock

Discover the perfect rural retreat in this beautifully appointed dog friendly barn set in AONB. Blending rustic character with modern convenience & offering a unique lifestyle opportunity for those seeking space, comfort & dedicated environment for their pets Standout feature of Hare Barn is the impressive 3/4 acre private paddock . Fully enclosed & well maintained providing a safe expansive space for all dogs to run freely or for those looking to enjoy countryside right at their doorstep

Top Guest favourite
A welcoming sitting room features a stone fireplace with neatly stacked logs beside it. Colorful furniture adds warmth, with a wooden table in the center displaying a backgammon set. The space is illuminated by natural light streaming through the window.
Cottage in Bibury
4.96 out of 5 average rating, 202 reviews

Comfortable Cotswold lodge conservatory and garden

Centrally located in a quiet corner in one of the most picturesque villages in the Cotswolds, Saltway Lodge in Bibury is a perfect escape for peace, quiet and fresh air... It is close to Cheltenham renowned (festival) race horse track, literature and jazz festivals as well as the annual airshow at Fairford and much more. The area has many wonderful markets, pubs, spas and walks all within easy reach. A step back in time to the Roman age and beyond but with up to date amenities!

Top Guest favourite
A dining table is set with a plate and glass, accompanied by cutlery. In the background, a comfortable sofa adorned with colorful cushions provides a cozy atmosphere, with natural light filtering through nearby windows.
Cottage in Winstone
4.96 out of 5 average rating, 238 reviews

Cotswold retreat. Spacious and peaceful

This rural retreat provides spacious, comfortable accommodation with fabulous views. An open plan ground floor leads to a south facing terrace (sole use.) Upstairs there is a huge bedroom ( Super King bed) and a roll top bath with garden view. Shower/WC downstairs Private parking. Hosts on hand if required. This peaceful rural village is an ideal base to explore the Cotswolds and soak up glorious countryside. Enjoy excellent dog walking and cycling straight out of the door.

Top Guest favourite
A private courtyard garden is surrounded by lavender plants, with a white picket fence framing the scene. A round table is accompanied by four wicker chairs, providing a serene outdoor space. Natural light bathes the brick exterior of The Little Retreat.
Cottage in Worcestershire
5 out of 5 average rating, 176 reviews

Dog friendly stylish cottage near Malvern Hills

The Little Retreat is a beautiful stable conversion. The open plan living/kitchen/dining room has a vaulted ceiling, stylish lighting and everything you need to cook up a storm. With cosy underfloor heating throughout, this is a special place, with only 5 star reviews! The Malvern Hills, and the new Cotswold Designer Outlet are on the doorstep, the Cotwolds Hills, Jeremy Clarkson's pub and Diddly Squat Farm are less than an hour away. Well behaved dogs welcome by arrangement.

Top Guest favourite
A charming stone cottage is framed by lush greenery and colorful flowering plants. A wooden gate leads to a gravel driveway, while rolling hills can be seen in the background under a clear blue sky.
Cottage in Stanton
5 out of 5 average rating, 138 reviews

Hobleys Cottage Stanton Nr Broadway

Hobleys Cottage is positioned on the edge of the historic village of Stanton which is widely regarded as one of the most picturesque in the Cotswolds. Recently refurbished the luxury accommodation is light and spacious with a well-equipped kitchen, open plan dining and sitting room. Wake up to stunning views over the adjoining pasture fields; a relaxing setting and a perfect base from which to explore the Cotswalds. The village pub The Mount Inn is within walking distance.

Guest favourite
A modern kitchen features sleek grey cabinetry and polished white countertops. A stainless steel sink is complemented by a built-in wine fridge. Nearby, large glass doors open to a garden area, allowing natural light to illuminate the space. A decorative welcome sign is placed on the countertop.
Cottage in Winchcombe
4.92 out of 5 average rating, 559 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!

Popular amenities for Cheltenham cottage rentals

Quick stats about cottage rentals in Cheltenham

  • Total holiday rentals

    Explore 20 holiday rentals in Cheltenham

  • Nightly prices starting at

    Cheltenham holiday rentals start at $104 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,310 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Cheltenham holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Cheltenham rentals

  • 4.8 Average rating

    Cheltenham stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Cheltenham's top spots, include Cheltenham Racecourse, Pittville Park, and Everyman Theatre

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