Cottages in Cheltenham

Within 10 miles
  • Within 1 mile
  • Within 2 miles
  • Within 3 miles
  • Within 5 miles
  • Within 10 miles
  • Within 20 miles
  • Within 30 miles
  • Within 50 miles
1
2
0
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
0
0
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
0
0
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
0
0
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
Pets
  • Pets
  • 1
  • 2
  • 3
  • 4
  • 5
  • 6
  • Property pet free
7
  • 7
  • 3
  • 4
  • -
  • 2
  • 5
  • 6
  • 8
  • 9
  • 10
  • 11
  • 12
  • 13
  • 14
  • 15
  • 16
  • 17
  • 18
  • 19
  • 20
  • 21
  • 22
  • 23
  • 24
  • 25
  • 26
  • 27
  • 28
3 Days +/-
  • Exact Dates
  • 1 Day +/-
  • 2 Days +/-
  • 3 Days +/-

British Travel Award Winners!

We are delighted to announce that we have been awarded 'Best UK Holiday Cottage/Self Catering Booking Company' at the British Travel Awards.

Cottages in Cheltenham

REFINE SEARCH

Your Cheltenham, Gloucestershire search returned 62 cottages

Most relevant
  • Distance to Location
  • Most relevant
  • Price (lowest first)
  • Price (highest first)
  • Sleeps (lowest first)
  • Sleeps (highest first)
  • Tick Rating (lowest first)
  • Tick Rating (highest first)
20
  • 10
  • 20
  • 50
  • 100
Map View
Brooklands - 988712 - photo 1
1 of 32
32
Chedworth, Cotswolds, GL54
  • Sleeps2
  • Bedrooms2
  • PetsNo

    4.3★

    Good

  • Sykes rating

Enchanting cottage with incredible views. Gorgeous, romantic bolt hole. Heavenly. (Ref. 988712)

  • Wi-fi
  • Washing machine

7 nights from £440

See more details
Little Noo - 1169113 - photo 1
1 of 16
16
Gloucester, Gloucestershire, GL4
  • Sleeps5
  • Bedrooms3
  • PetsNo

  • Sykes rating

Beautiful terraced cottage in Upton St Leonards. AGA, roll-top bath. Lovely walks from the doorstep. Village pub and well-stocked farm shop within walking distance. Gloucester 2 miles. (Ref. 1169113)

  • Wi-fi
  • Off-road parking
  • Washing machine
  • Baby-friendly

7 nights from £461

See more details
Hammonds Farmhouse - 1134526 - photo 1
1 of 85
85
Stroud, Cotswolds, GL6
  • Sleeps16
  • Bedrooms8
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Hammonds Farmhouse, a stunning home resting in the outskirts of the town of Stroud in Gloucestershire. In AONB. Woodburning stove. Countryside views. Stonehouse 4.9 miles; Gloucester 9.9 miles; Cheltenham 12.5 miles. (Ref. 1134526)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room

7 nights from £3024

See more details
Hetty's Stables - 1091364 - photo 1
1 of 30
30
Aylworth nr Naunton, Cotswolds, GL54
  • Sleeps7
  • Bedrooms3
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Peacefully located in the hamlet of Aylworth, close to Naunton, rests Hetty’s Stables which is a stunning barn conversion in the grounds of Aylworth Cottage. Underfloor heating. Woodburning stove. WiFi. Off-road parking. En-suite bedrooms. Naunton 1.5 miles; Bourton-on-the-Water 4.1 miles; Stow-on-the-Wold 6.8 miles. (Ref. 1091364)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £956

See more details
Postmaster's Lodging - 976759 - photo 1
1 of 33
33
Winchcombe, Cotswolds, GL54
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Postmasters Lodging is set over three floors in Winchcombe, Cotswolds. Open-plan living area. Cheltenham 8 miles; Broadway 9 miles. (Ref. 976759)

  • Wi-fi
  • Dishwasher
  • Baby-friendly

7 nights from £708

See more details
Greystones - 1135285 - photo 1
1 of 40
40
Upton St Leonards, Gloucestershire, GL4
  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A beautifully-decorated, four-bedroom abode residing in Upton St. Leonards, Gloucestershire. Games room. Off-road parking for 3 cars due to private drive. Close to amenities. In an AONB. Pretty views. Gloucester 3.1 miles. (Ref. 1135285)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room

7 nights from £1138

See more details
The Nook - 1103863 - photo 1
1 of 26
26
Jack's Green near Painswick, Cotswolds, GL6
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A wonderful cottage resting in Jack's Green, Gloucestershire. Woodburning stoves. Freestanding bath. AGA. Countryside views. Stroud 4.7 miles; Gloucester 9.4 miles; Cheltenham 10.1 miles. (Ref. 1103863)

  • Wi-fi
  • Off-road parking
  • Washing machine

7 nights from £706

See more details
Spring Cottage - 1172247 - photo 1
New property
1 of 20
20
Birdlip near Brockworth, Cotswolds, GL4
  • Sleeps4
  • Bedrooms2
  • PetsYes

  • Sykes rating

Spring cottage is a delightful, pet-friendly holiday cottage resting in the village of Birdlip near Brockworth in Gloucestershire with an electric fire. Gloucester 7.4 miles; Cheltenham 5.9 miles (Ref. 1172247)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher

7 nights from £529

See more details
The Alms House East - 1159773 - photo 1
1 of 34
34
Forthampton near Tewkesbury, Gloucestershire, GL19
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Alms House West is a delightful holiday home located on the outskirts of the village of Forthampton in Gloucestershire with a toasty woodburning stove. Ledbury 12.1 miles; Gloucester 12.3 miles; Cheltenham 12.6 miles; Malvern 12.4 miles. (Ref. 1159773)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £601

See more details
Cotswold Outlet Coach House - 1163701 - photo 1
Offer
1 of 27
27
Tewkesbury, Gloucestershire, GL20
  • Sleeps4
  • Bedrooms2
  • PetsYes

  • Sykes rating

Cotswold Outlet Coach House is a charming holiday coach house resting in the historical town of Tewkesbury in Gloucestershire that welcomes one pet. Cheltenham 8.6 miles; Gloucester 12 miles; Malvern 16.6 miles; Ledbury 19.2 miles (Ref. 1163701)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

  • 20% off - Sat 31st May to 7th Jun 2025

  • 20% off - Sat 14th Jun to 21st Jun 2025

  • 20% off - Sat 21st Jun to 28th Jun 2025

  • 20% off - Sat 28th Jun to 5th Jul 2025

  • 20% off - Sat 5th Jul to 12th Jul 2025

  • 20% off - Sat 12th Jul to 19th Jul 2025

  • 20% off - Sat 19th Jul to 26th Jul 2025

  • 20% off - Sat 26th Jul to 2nd Aug 2025

  • 20% off - Sat 2nd Aug to 9th Aug 2025

  • 20% off - Sat 9th Aug to 16th Aug 2025

  • 20% off - Sat 16th Aug to 23rd Aug 2025

  • 20% off - Sat 23rd Aug to 30th Aug 2025

  • 20% off - Sat 30th Aug to 6th Sep 2025

7 nights from £494

Last booked yesterday
See more details
The Granary - 1140060 - photo 1
1 of 29
29
Bourton-On-The-Water, Cotswolds, GL54
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

The Granary is a charming, barn conversion based in Naunton near Bourton-on-the-Water, Gloucestershire. Ground-floor living. Pet-friendly. In an AONB. Stow-on-the-Wold 7.1 miles; Moreton-in-Marsh 11.4 miles; Cheltenham 12.9 miles; Chipping Norton 16.2 mil (Ref. 1140060)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £598

See more details
Thatchers Barn - 1050562 - photo 1
1 of 28
28
Toddington, Gloucestershire, Gl54
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A unique, detached barn conversion found on 14 acres of beautiful land on the outskirts of Toddington, Gloucestershire. Lake. Woodburning stove. Jukebox. Evesham 9.1 miles; Cheltenham 11.7 miles; Gloucester 19.3 miles. (Ref. 1050562)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £534

See more details
Fern Cottage - 1012253 - photo 1
1 of 26
26
Winchcombe, Cotswolds, GL54
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

This is a mid-terrace cottage situated in the town of Winchcombe, Gloucestershire in the Cotswolds. Enclosed patio and garden. One well-behaved dog welcome. Traditional features. Cheltenham 8.5 miles; Bourton-on-the-Water 11miles. Gloucester 15.6 miles. (Ref. 1012253)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from £902

See more details
Thimble Cottage - 1050024 - photo 1
1 of 35
35
Winchcombe, Cotswolds, GL54
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A charming terraced cottage situated in the centre of Winchcombe. Pet-friendly. Woodburning stove. Private garden. WiFi. Cheltenham 8.2 miles; Gloucester 15.3 miles. (Ref. 1050024)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £606

See more details
Hazel Manor Wing - 988694 - photo 1
1 of 43
43
Painswick, Cotswolds, GL6
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

A very smart and spacious country retreat! Set in the grounds of a large Cotswolds' manor - you are in a beautiful location and some good pubs near too. (Ref. 988694)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £691

Last booked yesterday
See more details
River Cottage - 988216 - photo 1
1 of 21
21
Tewkesbury, Gloucestershire, GL20
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A 14th century, Grade II listed property situated within the town of Tewkesbury. Along the River Avon. Enclosed rear garden. Pub within a 2-minute walk. Cheltenham 9 miles; Gloucester 11 miles. (Ref. 988216)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Sky TV

7 nights from £429

See more details
Gleed Cottage - 1091196 - photo 1
1 of 26
26
Naunton, Cotswolds, GL54
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5★

    Outstanding

  • Sykes rating

A homely, traditional Cotswold stone property, set across three floors in the peaceful village of Naunton, Gloucestershire. Enclosed garden. Dog-friendly. Bourton-on-the-Water 4.2 miles; Stow-on-the-Wold 5.4 miles; Cheltenham 12.8 miles. (Ref. 1091196)

  • Wi-fi
  • Dishwasher
  • Baby-friendly

7 nights from £483

Last booked 2 days ago
See more details
The Compton Cottage - 1100672 - photo 1
1 of 31
31
Northleach, Cotswolds, GL54
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

Outstanding Cottage in the rolling Cotswolds' countryside. A beautifully crafted cottage for 4 people, good pubs nearby and Cheltenham a short drive away. Perfect retreat! (Ref. 1100672)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Sky TV

7 nights from £858

See more details
Oyster Barn - 1091282 - photo 1
1 of 27
27
Naunton, Cotswolds, GL54
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A charming converted barn nestled in the peaceful Cotswold village of Naunton. WiFi. Woodburning stove. Dog-friendly. Child-friendly. Parking. Bourton-on-the-Water 4.4 miles; Stow-on-the-Wold 5.7 miles; Cheltenham 12.6 miles. (Ref. 1091282)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £683

Last booked 2 days ago
See more details
The Alms House West - 1120768 - photo 1
1 of 34
34
Tewkesbury, Gloucestershire, GL19
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A beautiful cottage set next to a picturesque church in the village of Forthampton, Gloucestershire. Rural position. Hill views. Pet-friendly. Gloucester 12.3 miles; Cheltenham 12.7 miles. (Ref. 1120768)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £601

See more details
Map View

This range of Cheltenham accommodation rests within one of the UK's best-preserved spa towns, promising a holiday experience to remember.

Why Cottages in Cheltenham?

This town, on the western fringes of the Cotswolds AONB, boasts elegant streets lined with Regency architecture, with one of the finest examples being the Pitville Pump Room. Other popular attractions include Cheltenham's Museum and Art Gallery know, The Holst Birthplace Musuem as well as the stylish Montpellier district of the town, a region full of beautiful buildings, boutique shops and restaurants. To discover the best things to do near your Cheltenham cottage, browse through our Cheltenham Travel Guide.

Places to visit near Cheltenham

Cottages in Cheltenham rest at the western gateway to the Cotswolds, making them ideally placed to explore this beautiful Area of Outstanding Natural Beauty. Avid ramblers will be in their element throughout the beauty of the Cotswolds, with many paths and trails coming surrounded by luscious greenery. You will also stumble across a choice of historic and characterful market towns, as well as an assortment of quaint little villages. During your Cheltenham cottage holiday, you may consider visiting popular spots such as Bourton-on-the-Water, Chipping Campden, Gloucester, Moreton-in-Marsh, Stow-on-the-Wold and Stroud.

Types of Cotswolds Holidays

If you're looking to explore the beauty of the Cotswolds on your next trip, find different holiday types to find a perfect break for you. Book a Cotswolds family holiday if you're looking to celebrate that special occasion, or treat yourselves to that extra touch with a choice of luxury Cotswolds cottages. For a unique holiday experience, try a glamping pod in Gloucestershire or Glamping pod in the Cotswolds. You can also choose from these dog-friendly cottages in the Cotswolds.

The wide variety of properties and experience of Sykes will ensure that your adventure is one to remember.