Best Vacation Homes in Cheltenham
Cottage
10.0(177 Reviews)
2 Bedrooms
1 Bath
3 Guests
613 ft²
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
US $229/Night
7 Nights - US $1,606
House
10.0(84 Reviews)
2 Bedrooms
1 Bath
3 Guests
344.45 ft²
- Fireplace/Heating
- Balcony/Terrace
Parking
Internet
US $141/Night
7 Nights - US $989
US $258/Night
7 Nights - US $1,809
Cottage
10.0(153 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $307/Night
7 Nights - US $2,146
Cottage
10.0(128 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
Ocean View- Balcony/Terrace
View
US $233/Night
7 Nights - US $1,632
Cottage
10.0(102 Reviews)
5 Bedrooms
5 Baths
10 Guests
2239 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $870/Night
7 Nights - US $6,091
Cottage
10.0(90 Reviews)
2 Bedrooms
2 Baths
4 Guests
753 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $287/Night
7 Nights - US $2,006
Cheltenham Luxury Rentals
New
House
9 Bedrooms
9 Baths
32 Guests
- Fireplace/Heating
- Pet Friendly
Air Conditioner- Internet
Unlock the Best Price
Cottage
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $5,799/Night
7 Nights - US $40,591
House
9.8(5 Reviews)
9 Bedrooms
6 Baths
24 Guests
107639.1 ft²
Private Pool
Oceanfront
Hot Tub- Fireplace/Heating
US $4,075/Night
7 Nights - US $28,525
Cabin
12 Bedrooms
12 Baths
22 Guests
- Fireplace/Heating
- Balcony/Terrace
- Parking
- Internet
US $3,829/Night
7 Nights - US $26,800
Apartment
9.4(23 Reviews)
6 Bedrooms
3 Baths
12 Guests
2142.02 ft²
- Fireplace/Heating
- View
- Parking
- Internet
US $3,800/Night
7 Nights - US $26,600
House
6 Bedrooms
5 Baths
12 Guests
10764 ft²
- Fireplace/Heating
Pool- Balcony/Terrace
- Pet Friendly
US $3,655/Night
7 Nights - US $25,586
Apartment
6 Bedrooms
1 Bath
12 Guests
- Private Pool
- Hot Tub
- Pool
- Pet Friendly
US $3,093/Night
7 Nights - US $21,654
Cheltenham Pet Friendly Vacation Rentals
Cottage
10.0(72 Reviews)
3 Bedrooms
1 Bath
7 Guests
1292 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $440/Night
7 Nights - US $3,080
House
10.0(7 Reviews)
3 Bedrooms
4 Baths
6 Guests
1022.57 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $459/Night
7 Nights - US $3,211
House
10.0(3 Reviews)
1 Bedroom
1 Bath
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
US $623/Night
7 Nights - US $4,364
House
10.0(57 Reviews)
4 Bedrooms
3 Baths
8 Guests
1938 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $618/Night
7 Nights - US $4,328
House
10.0(5 Reviews)
4 Bedrooms
4 Baths
10 Guests
- Fireplace/Heating
- View
- Pet Friendly
- Parking
US $408/Night
7 Nights - US $2,856
Cottage
10.0(35 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $582/Night
7 Nights - US $4,077
Cottage
10.0(34 Reviews)
6 Bedrooms
5 Baths
14 Guests
25575 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $1,888/Night
7 Nights - US $13,218
Cottage
10.0(31 Reviews)
2 Bedrooms
1 Bath
4 Guests
958 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $290/Night
7 Nights - US $2,028
Cheltenham Large Vacation Homes
House
10.0(28 Reviews)
4 Bedrooms
4 Baths
11 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $737/Night
7 Nights - US $5,159
Villa
10.0(8 Reviews)
4 Bedrooms
3 Baths
8 Guests
1732.99 ft²
- Fireplace/Heating
- View
- Parking
- Internet
US $553/Night
7 Nights - US $3,872
House
10.0(24 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $1,089/Night
7 Nights - US $7,621
Apartment
10.0(6 Reviews)
5 Bedrooms
4 Baths
12 Guests
1657.64 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Parking
US $774/Night
7 Nights - US $5,417
Cottage
10.0(19 Reviews)
4 Bedrooms
4 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $2,490/Night
7 Nights - US $17,427
Cottage
10.0(13 Reviews)
6 Bedrooms
6 Baths
12 Guests
2852 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $1,287/Night
7 Nights - US $9,006
Cottage
10.0(12 Reviews)
3 Bedrooms
2 Baths
12 Guests
2971 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $955/Night
7 Nights - US $6,688
House
10.0(5 Reviews)
5 Bedrooms
4 Baths
11 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,118/Night
7 Nights - US $7,824
Why Choose Rent By Owner for your Cheltenham Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Cheltenham
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here ensures you can fully enjoy all that this charming destination has to offer, whether you're seeking the lively atmosphere of peak season or the tranquil beauty of quieter months.
Peak Season Highlights
June to August
During the summer months, this destination experiences its busiest period, attracting visitors who want to enjoy outdoor festivals and vibrant social events.
Average Temperature Daytime: 20°C to 24°C - Nighttime: 12°C to 15°C
December to February
The winter season draws travelers seeking festive celebrations and cozy retreats, making it a lively time for booking vacation rentals in the region.
Average Temperature Daytime: 5°C to 8°C - Nighttime: 0°C to 3°C
Off-Season Highlights
March to May
Springtime offers milder weather and fewer crowds, providing an ideal opportunity to explore the area at a relaxed pace with preferred vacation rentals available.
Average Temperature Daytime: 10°C to 15°C - Nighttime: 3°C to 7°C
September to November
Autumn brings cooler temperatures and quieter streets, making it an excellent time for visitors looking for tranquility in their stay.
Average Temperature Daytime: 14°C to 19°C - Nighttime: 7°C to 11°C
Weekly Weather Forecast for Cheltenham
How to Book Your Cheltenham Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Cheltenham
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor seating areas perfect for relaxing and dining amidst the scenic surroundings.
- Take advantage of private gardens or landscaped yards to unwind in nature during your stay.
- Make the most of nearby walking trails or cycling paths that showcase the area's natural beauty.
- Benefit from access to outdoor patios or decks ideal for social gatherings or morning coffees.
- Discover outdoor recreational facilities such as lawns or play areas suitable for families and children.
- Experience outdoor lighting features that allow you to enjoy the area’s charm after sunset.
- Utilize communal outdoor spaces like shared gardens or courtyards available at certain properties here.
Top Attractions Around Cheltenham
What attractions are nearby?
In this charming area, you can enjoy a variety of activities such as exploring historic landmarks, strolling through picturesque parks, and experiencing the vibrant local culture—all conveniently accessible from your vacation rental in Cheltenham.
Family Activities
- Cheltenham Racecourse: Enjoy a family day out by experiencing thrilling horse racing events that bring excitement and entertainment to all ages.
- The Wilson Art Gallery and Museum: Explore engaging exhibits and interactive displays that showcase the area's rich cultural heritage and history, perfect for curious young minds.
- Imperial Gardens: Relax and unwind in beautifully landscaped gardens that offer scenic views and plenty of space for children to play and explore.
- Birdland Park and Gardens: Discover exotic birds and lush gardens, providing an educational and captivating experience for families visiting this charming destination.
Adult Activities
- Relaxing Spa Days: Indulge yourself at one of the region's renowned spa centers to unwind and enjoy rejuvenating treatments amidst serene surroundings.
- Golfing Experiences: Play a round at top-rated golf courses nearby, where you can enjoy beautiful landscapes and challenging fairways tailored for all skill levels.
- Cultural Heritage Tours: Explore the local museums, historic sites, and art galleries that showcase the area's rich history and vibrant cultural scene.
- Fine Dining in the Area: Savor exquisite cuisine at some of the region’s finest restaurants, offering a variety of culinary delights to enhance your stay.
Other Places to Stay in Cheltenham
Cotswold District
Charlton Kings
Lower Slaughter
Great Rissington
Tewkesbury District
Bourton-on-the-Water
Stow-on-the-Wold
Winchcombe
Little Rissington
Northleach
Montpellier
Temple Guiting
Cheltenham Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Visit Around Local Events: Check the area's event calendar to coincide your stay with festivals or markets, enhancing your experience of the local culture.
- Explore Nearby Natural Attractions: Take time to discover the scenic parks and green spaces around here for outdoor activities and relaxation amidst beautiful surroundings.
- Discover Authentic Local Cuisine: Sample the region’s traditional dishes at nearby restaurants or food markets to get a real taste of this destination’s culinary heritage.
- Utilize Convenient Transportation Options: Familiarize yourself with the accessible transit routes and walking paths to easily explore the best sights and hidden gems here.
Transportation Options
- Train Services: The town's train station offers direct links to major UK cities, making it convenient to explore the region or arrive at your vacation rental in Cheltenham with ease.
- Bus Network: A comprehensive bus system connects the area to surrounding towns and attractions, providing an affordable and flexible transportation option during your stay.
- Taxis and Ride-Sharing: Private taxis and popular ride-sharing services are readily available, offering door-to-door convenience for quick travel around this destination.
- Car Rentals: Local car rental agencies provide the freedom to explore the scenic countryside and nearby points of interest at your own pace while staying close to your vacation rental.
Local Customs Options
- Afternoon Tea Traditions: In this region, enjoying a traditional afternoon tea with scones and clotted cream is a cherished custom that you can experience during your stay.
- Local Punting Etiquette: When exploring the area by boat, it's customary to follow specific rules of etiquette on the river, such as yielding to other vessels and respecting historical navigation practices.
- Regency Style Celebrations: The area's rich Regency history means that participating in or observing period-inspired events and festivals adds a unique cultural dimension to your visit.
- Tea Room Hospitality: Visiting local tea rooms offers an authentic glimpse into how residents here socialize and welcome visitors with warm hospitality and traditional treats.
Cheltenham Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Cheltenham?
There are a lot of options in Cheltenham. If you plan on staying in the Cheltenham area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Cheltenham:
- Enchanting Grade II listed,Log Burner,allocated parking,town centre but secluded
- Unique & Characterful 16th Century Cottage w/own driveway 2 Min Walk to Village!
- Delightful, barn cottage in peaceful rural village. Walks, pubs, scenery. Relax!
- Kingfisher Cottage - sleeps 10 guests in 5 bedrooms
- Lovely Cotswold holiday Barn within walking distance of restaurants/shops
- Lovely Cotswold holiday cottage within walking distance of restaurants/shops
- The Annexe @The Oaks
- Teagles Cottage - a delightful home from home in Stow-on-the-Wold
- SPRING COTTAGE Family and Pet Friendly Cosy Cottage in the heart of the Village
- Charming Victorian Wool Cottage on the Cotswold Way in Winchcombe.
2. How many vacation rentals have private pools in Cheltenham?
There are 7 vacation rentals with private pools near Cheltenham. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Cheltenham are best for families?
If you are looking for a family-friendly vacation home in Cheltenham, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Cheltenham:
4. How many Rentbyowner vacation rentals are available in Cheltenham?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 2108 in the Cheltenham area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Cheltenham.
5. What is the cancellation policy for vacation rentals in Cheltenham?
Cancellation policies vary depending on the host and property listing. It’s recommended to review the specific cancellation terms on the listing page or contact the property owner directly to understand your options before booking.
6. Are there any minimum stay requirements for vacation rentals in Cheltenham?
Minimum stay requirements differ from property to property. Be sure to check the details of each listing to confirm any minimum night policies applicable here, especially during peak travel seasons.
7. How do I find accessible vacation rentals in Cheltenham suited to specific needs?
Accessible properties are listed with detailed descriptions of their features. You can filter search results based on accessibility amenities or reach out directly to the host to ensure the accommodation meets your requirements.
8. What amenities should I expect in vacation rentals in Cheltenham?
Most listings provide comprehensive information about amenities such as Wi-Fi, parking, kitchens, and more. To confirm that the property has everything you need, review the amenities section of the listing or contact the host for additional details.
9. How can I ensure a smooth check-in process when staying in Cheltenham vacation rentals?
Check-in procedures are outlined in each listing, with many offering flexible options like self-check-in. For a seamless experience, communicate with the host ahead of time if you have special requirements or need further instructions.
Cheltenham Top Rated Vacation Rentals
House
10.0(3 Reviews)
9 Bedrooms
6 Baths
24 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $2,836/Night
7 Nights - US $19,849
House
10.0(2 Reviews)
6 Bedrooms
4 Baths
12 Guests
2153 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $2,364/Night
7 Nights - US $16,550
Hotel
9.2(659 Reviews)
6 Baths
251.15 ft²
- Private Pool
- Hot Tub
Spa- Fireplace/Heating
US $300/Night
7 Nights - US $2,102
US $537/Night
7 Nights - US $3,756
US $265/Night
7 Nights - US $1,856
US $123/Night
7 Nights - US $864
US $361/Night
7 Nights - US $2,530
Hotel
8.8(485 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
US $282/Night
7 Nights - US $1,973
