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.

24/7 “On Holiday” Support

Our friendly UK team are here to help, in case of any emergency.

Award Winning Holiday Experts

Over 30 years of experience in UK self-catering holidays.

B Corp Certified Business

Committed to making a positive social and environmental impact.

Safe & Secure Payments

Flexible payment options for peace of mind.

Cottages in Cheltenham

REFINE SEARCH

Your Cheltenham, Gloucestershire search returned 60 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
Hazel Manor Wing - 988694 - photo 1
33
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

See more details
Beechnut Cottage - 952307 - photo 1
26
Tewkesbury, Gloucestershire, GL20
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A stylish ground-floor cottage resting in Aston on Carrant, Tewkesbury. Open-plan living. Ideal for couples. Tewkesbury 4 miles. Malvern Hills Area of Outstanding Natural Beauty 20.8 miles. (Ref. 952307)

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

7 nights from £363

See more details
Jackdaw's Roost - 991352 - photo 1
25
Cheltenham, Gloucestershire, GL19
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

This quaint adult only country cottage is situated in The Leigh, Gloucestershire. Woodburner. Pet-friendly. Period features. Tewkesbury 9.5 miles; Cirencester 14.7 miles. (Ref. 991352)

  • Off-road parking
  • Ground floor bedroom
  • Washing machine

7 nights from £374

See more details
Thatchers Barn - 1050562 - photo 1
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
The Nook - 1103863 - photo 1
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 £718

See more details
Wellinghill Lodge - 1010167 - photo 1
27
Cheltenham, Cotswolds, GL52
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A stunning, detached lodge situated in Cheltenham, Cotswolds. WiFi. Pet-friendly. Open-plan living. Tewkesbury 5.9 miles; Cirencester 14.7 miles. (Ref. 1010167)

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

7 nights from £403

See more details
Five Mile House Barn - 1014891 - photo 1
31
Duntisbourne Abbots near Cirencester, Cotswolds, GL7
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

A characterful, Grade II listed dwelling, resting on the outskirts of Cirencester. Woodburning stove. Pets welcome. Stroud 12.8 miles; Gloucester 14.9 miles. (Ref. 1014891)

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

7 nights from £609

See more details
The Old Cider House - 948400 - photo 1
18
Prestbury near Cheltenham, Cotswolds, GL52
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Beautiful Cotswold stone character property set on 150-acre equestrian centre. En-suite shower room. WiFi. Country walks and equestrian activities on site. 10 minutes to Cheltenham, 7 minutes to Cheltenham racecourse. (Ref. 948400)

  • Wi-fi
  • Off-road parking

7 nights from £462

See more details
Lower Pack Horse Cottage - 1131021 - photo 1
New property
42
Winchcombe, Cotswolds, GL54
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Lower Pack Horse Cottage is a harmonious Grade-II listed cottage in the town of Winchcombe in Gloucestershire, boasting a woodburning stove and a Smart TV. Cheltenham 7.7 miles; Broadway 10 miles; Gloucester 16.8 miles. (Ref. 1131021)

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

7 nights from £629

Last booked 2 days ago
See more details
Old Sorting Office - 977985 - photo 1
13
Winchcombe, Cotswolds, GL54
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

This historic ground floor apartment is located in Winchcombe, Gloucestershire. Romantic. Spacious rooms. Open-plan living. Cheltenham 8 miles; Broadway 9 miles. (Ref. 977985)

  • Wi-fi
  • Ground floor bedroom
  • Baby-friendly

7 nights from £478

See more details
Postmaster's Lodging - 976759 - photo 1
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
Hammonds Farmhouse - 1134526 - photo 1
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 £3026

Last booked yesterday
See more details
Hetty's Stables - 1091364 - photo 1
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
Beeches Studio - 30299 - photo 1
26
Cranham near Gloucester, Cotswolds, GL4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

First floor studio accommodation in Cranham village. WiFi, easy access to walking and woodland, raised decking perfect for relaxing. Gloucester 5 miles. (Ref. 30299)

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

7 nights from £343

See more details
River Cottage - 988216 - photo 1
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

Last booked yesterday
See more details
Spring Cottage - 1132436 - photo 1
32
Stroud, Cotswolds, GL6
  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A beautiful property set just outside the town of Stroud, Gloucestershire. Reverse level accommodation. Tasteful furnishings. Barbecue. Gloucester 14.3 miles; Cirencester 14.4 miles. (Ref. 1132436)

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

7 nights from £636

See more details
The Gables - 1116058 - photo 1
46
Sheepscombe, Cotswolds, GL6
  • Sleeps8
  • Bedrooms4
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A beautiful four-bedroom holiday home resting in Sheepscombe, Gloucestershire. Hot tub. Stunning panoramic views.Off-road parking. Stroud 4.7 miles; Gloucester 9.4 miles; Cheltenham 10.1 miles. (Ref. 1116058)

  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher

7 nights from £1495

See more details
Fern Cottage - 1012253 - photo 1
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 £816

Last booked yesterday
See more details
Under Catswood - 1066428 - photo 1
46
Elcombe near Stroud, Cotswolds, GL6
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

Under Catswood is a stunning, detached single storey dwelling resting in Elcombe near Stroud, Gloucestershire. Open-plan. WiFi. Smart TV. Gardens. Secluded. Off-road parking. Woodburning stove. Painswick 4.8 miles; Gloucester 10.5 miles. (Ref. 1066428)

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

7 nights from £1154

Last booked yesterday
See more details
Runnymede - 1071199 - photo 1
38
Tewkesbury, Gloucestershire, GL20
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A charming Grade II listed cottage resting in the historic riverside town of Tewkesbury, Gloucestershire. Pet-friendly. Enclosed garden. Close to amenities. Cheltenham 10 miles; Gloucester 11.7 miles; Malvern 13.2 miles. (Ref. 1071199)

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

7 nights from £641

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.