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
  • -
  • 1
  • 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 Awards 2025 Award

British Travel Award Winners!

We’re proud to share that we’ve been recognised in the 2025 British Travel Awards as the Silver Winner for Best Company for UK Holiday Home Rentals.

Cottages in Cheltenham

REFINE SEARCH

Your Cheltenham, Gloucestershire search returned 73 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
A street with shops and buildings made of stone and brick at Postmaster's Lodging in Winchcombe
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


for 7 nights £716

Last booked 1 hour ago
See more details
A row of houses with stone and brick walls blue doors and windows and small planters on the sidewalk at Lower Pack Horse Cottage in Winchcombe
42
Winchcombe, Cotswolds, GL54
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • 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


for 7 nights £761

See more details
A wooden building with potted plants and gravel driveway at Wellinghill Lodge in Cheltenham
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


for 7 nights £380

See more details
The Garden Retreat - 1159770 - photo 1
32
Winchcombe, Cotswolds, GL54
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

8 Gloucester Street is a charming house in Winchcombe, Gloucestershire, situated in the Cotswolds, boasting a woodburning stove and an enclosed garden. Cheltenham 7.8 miles; Broadway 8.4 miles; Gloucester 14.7 miles. (Ref. 1159770)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £521

Last booked yesterday
See more details
A dining table set with plates and cutlery and a bouquet of flowers next to a living area with a leather sofa a wooden chair a TV and large window at The Coach House in Cheltenham
23
Cheltenham, Gloucestershire, GL51
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

An idyllic first-floor apartment nestled in the heart of Cheltenham, Gloucestershire. Romantic. Central location. Close to local amenities. Close to Cotswolds AONB. Private patio. Tewkesbury 8.2 miles; Cirencester 16 miles; Stratford-upon-Avon 31.8 miles. (Ref. 1121786)

  • Wi-fi
  • Washing machine


for 7 nights £426

See more details
A front yard with a door and light fixtures at The Old Sorting Office in
14
Winchcombe, Cotswolds, GL54
  • Sleeps2
  • Bedrooms1
  • PetsYes

  • 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. 1183136)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

  • 20% off - Fri 13th Mar to 24th Mar 2026


for 7 nights £443

See more details
An outdoor area with a round table and four chairs with cushions on grass outside a stone building with windows and a door at The Compton Cottage in Northleach
31
Northleach, Gloucestershire, 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


for 7 nights £930

See more details
An exterior view of a house surrounded by trees and a fence at Wellinghill Cottage at Wellinghill House Charlton Kings
33
Cheltenham, Cotswolds, GL52
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Wellinghill Cottage is a superb barn conversion in Charlton Kings, Gloucestershire, with alpacas onsite and a woodburning stove. Cheltenham 3.1 miles; Gloucester 13.5 miles; Cirencester 14.3 miles. (Ref. 1183374)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £465

Last booked yesterday
See more details
A side entrance to a brick house with a black metal gate with a Beechnt Cottage sign and a garden with green grass and trees in the background at Beechnut Cottage in Tewkesbury
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


for 7 nights £363

See more details
A wooden footbridge over a pond leading to a stone building with a tiled roof at Jackdaw's Roost in Cheltenham
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


for 7 nights £404

Last booked yesterday
See more details
A stone house with a large window extension and a gravel driveway at The Nook in Jack's Green near Painswick
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


for 7 nights £726

Last booked 2 days ago
See more details
A stone house with large windows and doors surrounded by grass and trees at Hetty's Stables in Aylworth nr Naunton
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 mil (Ref. 1091364)

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

  • £402 off - Fri 13th Mar to 20th Mar 2026

  • £455 off - Fri 20th Mar to 27th Mar 2026


for 7 nights £956

See more details
A stone farmhouse with a wooden pergola and outdoor seating surrounded by flowers and greenery at Hammonds Farmhouse in Stroud
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


for 7 nights £2911

See more details
A brick exterior of a house with two doors and windows with climbing plants and a white bench outside at River Cottage in Tewkesbury
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


for 7 nights £405

Last booked 2 days ago
See more details
A stone cottage with a gravel driveway and garden in front at Spring Cottage in Stroud
31
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

  • 10% off - Tue 6th Jan to 20th Mar 2026


for 7 nights £659

See more details
A building exterior with windows and grass at Flat 2 Battledown Grange in Cheltenham
27
Cheltenham, Gloucestershire, GL52
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Flat 2 Battledown Grange is a lovely, ground-floor holiday apartment resting in the charming town of Cheltenham in Gloucestershire near a shop and pub. Tewkesbury 9.7 miles; Cirencester 15.2 miles; Stratford-upon-Avon 30.4 miles. (Ref. 1175215)

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


for 7 nights £505

Last booked yesterday
See more details
A stone house exterior with potted plants on a paved patio and metal chairs with a table at The Old Cider House in Prestbury near Cheltenham
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


for 7 nights £474

See more details
Stone exterior of a barn with a green stable door open a wooden shutter and climbing ivy at Five Mile House Barn in Duntisbourne Abbots near Cirencester
31
Duntisbourne Abbots near Cirencester, Gloucestershire, 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


for 7 nights £659

See more details
A stone house with a tiled roof and black windows next to a wooden structure with a tiled roof in a garden at The Alms House East in Forthampton near Tewkesbury
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


for 7 nights £649

See more details
A single-story house with a tiled roof next to a driveway and palm trees at Hillside in Bishops Cleeve
28
Bishops Cleeve, Gloucestershire, GL52
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

Hillside is a homely, detached bungalow situated in a quiet residential area of Bishops Cleeve, Gloucestershire, featuring convenient ground-floor living. Cheltenham 5.9 miles; Tewkesbury 9 miles. (Ref. 1175869)

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


for 7 nights £476

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, Evesham, Gloucester, Moreton-in-Marsh, Tewkesbury, 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.