
Guesthouse vacation rentals in Cheltenham
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouses in Cheltenham
Guests agree: these guesthouses are highly rated for location, cleanliness, and more.

Luxury self-catering for two in the Cotswolds
Situated on a farm between the picturesque villages of Broadway and Winchcombe this private annex is the ideal getaway or escape for visiting the Cotswolds. Spread over two floors the open ground floor contains a small fully equipped kitchen and comfortable seating area with large wood burner. There is a private outdoor area for your enjoyment. Upstairs has a super king size bed and ensuite bathroom. All bedlinen is 100% cotton with down duvet, pillows soft towels and lots of wardrobe space.

Renovated cottage with views of Bredon Hill
Cedar Cottage is a recently renovated self contained cottage adjacent to our home with its own entrance and secure parking on site. It has everything you need to make your stay comfortable with high quality stylish furnishings including a king sized bed with Emma mattress. The village has 2 pubs and a village shop and is perfectly situated for easy access to Cheltenham Festivals, Upton-upon-Severn and the Cotswolds. Wonderful walks directly from the cottage. Bike storage & EV Charger available

Amberley Coach House, nr Stroud
Cosy self-contained room with comfy kingsize bed, double sofabed and en-suite shower on the upper floor of a separate building across the garden from the house. Beautiful Cotswolds village setting high on a hill between the towns of Nailsworth (2 miles) and Stroud (3 miles). Wifi. No kitchen facilities but there's a kettle and big coolbox. Moments from gorgeous National Trust common land. Three pubs, a hotel and a shop/café in the church within 5-20 minutes' walk. Step-free access via garden.

Cosy countryside retreat.
The Nest is a self contained detached annexe set in the peaceful Gloucestershire village of The Leigh. The property has been newly refurbished and is available for up to 2 people with access to a secluded garden space within our lovely orchard surroundings. The property has easy access and ample parking. Located within easy reach of Cheltenham, Tewkesbury, Gloucester, The Malverns, Cotswolds and M5, the accommodation is in a perfect position for exploring all that the area has to offer.

The Cotswolds Couples' Getaway
In the centre of beautiful Minchinhampton, this detached cosy cottage is open plan in design and tastefully renovated throughout with plenty of modern conveniences. Set in our quiet pretty garden, and with on-site parking + Type 2 EV charger, a perfect getaway. The space is safe for a couple, equipped for living, and it is easy to remain quite isolated from the busy world. As hosts, we are right next door for queries and information. Please read our reviews to see why people book.

Small Cotswold cottage / annex
Self-contained single-storey annex set in its own grounds. Newly decorated with off-road parking; south-facing garden with terrace. Ideal base for exploring the Cotswolds and minutes away from Burford and Jeremy Clarkson's pub, the Farmer’s Dog. Perfectly positioned to visit Bourton-on-the-Water, Stow-on-the-Wold and Bibury. 6 miles from RAF Brize Norton. Using non-toxic household products where possible and putting sustainability at the forefront by using refillable bottles.

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.

Beautiful Self-Contained Annexe in Cheltenham
A lovely, newly refurbished annexe, perfect for 1 or 2 guests within good distance to the town center. A cosy, fully functioning, self-contained home from home featuring a double bed, kitchenette, en suite bathroom, 32" TV, heated floor and radiator with a private entrance. Located a 30 minute walk from the town centre and the Brewery Quarter, which is full of restaurants and bars, 2 cinemas, Mr Mulligans Adventure Golf and Hollywood Bowl.

Two Double Bedrooms Guest Annexe with EV Charging
A 2 Bedroom guest annexe within 100 yards of Cheltenham Race Course and within a 10 minute walk to the Town Centre. This property is tucked in the grounds of the main house and offers secure gated parking. The accommodation comprises open plan living space with fantastic views of Cleeve Hill and two double bedrooms. Use of laundry facilities and home gym if required (Subject to Availability). EV Charging available (separate charge).

Cleeve Cottage (The Studio)
A small detached studio/annex, in the picturesque village of Bushley, ideal location for anyone looking to have a short break in the countryside just 1.5 miles from the old market town of Tewkesbury and only 20 minutes from Cheltenham so perfect for a weekend at the races. Plenty of stunning rural locations to be explored nearby, with easy access to the beautiful Malvern hills, fantastic for cycling and hiking

Mulberry is our self contained small town house
Located a short walk from the centre of Cheltenham, this small town house has its own entrance, a ground floor living space with discreetly concealed kitchen and a first floor double bedroom with an en suite luxury shower room. We have enhanced our cleaning routine and thoroughly disinfect all the property between visitors. We closely follow the AIRBNB and GOVERNMENT guidelines for the safety of us all.

Cotswold lodge with amazing views and famous walks
Enjoying spectacular views this 2 bedroom, dog friendly lodge sits on the top of Leckhampton Hill, enjoying easy access to the famous ‘Cotswold Way’ walk and is a 5 minute drive from the town centre of regency Cheltenham. The Lodge also includes a 3.5m outdoor kitchen looking over The Malvern Hills. The kitchen includes a large built in BBQ, a pizza oven and sink.
Popular amenities for Cheltenham guesthouses
Family-friendly guesthouses

Seedwood Barn

Doe Bank, Great Washbourne

Entire guesthouse set within Cotswold Water Park

Cotswold village location- Detached guest house

Meadow Lodge quiet annexe in countryside

Valleyside Annexe

Barn @ North Wraxall

B&B in Beautiful Cotswold Annex
Guesthouses with a patio

Little Rosewood is a Cosy Cotswold Retreat

Garden Annex Dormston

Prestbury Village Annexe.

Adorable One Bedroom Cotswold Studio

Country Barn / Cottage, Worcestershire

Gorgeous 1 Bed Cotswold rural studio. With Parking

Charming guest house in stunning wooded valley

The School House, Cambridge, Gloucestershire
Guesthouse rentals with a washer and dryer

Golden Stone Country Retreat, Cotswolds

Scenic 2 Bed Lodge with hot tub and indoor pool

Cosy Cotswold Lodge with Private Garden & Hot Tub

Gardener's Pavilion | Malvern

Blacklains Annexe, Birdlip, Cotswold

Self-contained property in Rodborough

Self-contained unit, parking & 3 mins walk to town

Greencourt Loft, Cotswold Way, Middleyard, Stroud
When is the best time to visit Cheltenham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $155 CAD | $150 CAD | $206 CAD | $161 CAD | $168 CAD | $161 CAD | $151 CAD | $155 CAD | $157 CAD | $174 CAD | $175 CAD | $151 CAD |
| Avg. temp | 5 °C | 5 °C | 7 °C | 9 °C | 12 °C | 15 °C | 18 °C | 17 °C | 15 °C | 11 °C | 7 °C | 5 °C |
Quick stats about guesthouse rentals in Cheltenham

Total vacation rentals
Explore 20 vacation rentals in Cheltenham

Nightly prices starting at
Cheltenham vacation rentals start at $84 CAD per night before taxes and fees

Verified guest reviews
Over 3,060 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Cheltenham vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Cheltenham rentals

4.9 Average rating
Cheltenham stays are highly rated by guests—averaging 4.9 out of 5!

Nearby attractions
Cheltenham’s top spots, include Cheltenham Racecourse, Pittville Park, and Everyman Theatre
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- Cotswolds AONB
- Oxford University
- Blenheim Palace
- Silverstone Circuit
- Lower Mill Estate
- West Midland Safari Park
- Cheltenham Racecourse
- Cadbury World
- Sudeley Castle
- Ludlow Castle
- Waddesdon Manor
- Bath Abbey
- Coventry Cathedral
- No. 1 Royal Crescent
- Puzzlewood
- Shakespeare's Birthplace
- Bowood House and Gardens
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- Hereford Cathedral
- Royal Shakespeare Theatre
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- Painswick Golf Club
- Dyrham Park
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