Big Cottages Cheltenham: Your Complete Planning Guide
Booking Big Cottages in Cheltenham gives you a perfect base to explore this elegant Regency spa town whilst enjoying the space and freedom that large holiday homes provide. The town sits on the edge of the Cotswolds with its honey-coloured stone villages and rolling hills just minutes away.
We think Cheltenham works brilliantly for group breaks because you get that rare combination of sophisticated town amenities alongside easy access to countryside walks and charming market towns. The properties range from grand period houses with enclosed gardens to modern self-catering villas with hot tubs and indoor pools.
Avoiding stress and planning the perfect group break
Which cottage?
Start with your absolute must-haves before you even look at properties. Set your budget first because rental costs for large groups can vary wildly between a basic 8 bed cottage and a massive country house that sleeps 20 with all the extras.
Location matters more than you think. Do you want to be walking distance from Cheltenham town centre or would you prefer a rural retreat in the Cotswolds? Consider how many bedrooms and bathrooms you actually need because a 10 bedroom property with two bathrooms creates queues nobody wants.
Decide early if you need dog friendly accommodation or prefer pet-free spaces. The modern versus rustic question affects everything from heating bills to whether your group will feel comfortable in the space.
Plan these in advance
How many bedrooms and bathrooms for your group
We always recommend one bathroom per four guests minimum. A property that sleeps 12 needs at least three bathrooms to avoid morning chaos. Check if bedrooms have ensuite facilities because that changes the dynamics completely for large holiday houses.
Bedroom allocation drama
Sort out who gets which room before you arrive. The master suite question causes more arguments than you'd expect. Consider drawing names from a hat or rotating rooms if you're booking for multiple nights to keep things fair.
Splitting costs between your group
Use apps like Splitwise to track who owes what. Decide upfront whether couples pay more than singles. Factor in that some guests might want the premium rooms and should pay accordingly for cottages to rent.
Deposits and getting reimbursed
One person typically books and pays the deposit for holiday cottages. Set clear expectations about when you need reimbursement. Most properties require full payment 6-8 weeks before arrival so chase people early.
Hidden fees
Check what's included in your rental price. Some holiday lets charge extra for heating and electricity. Linen and towels aren't always provided. Pet fees add up quickly for dog friendly properties. Last minute bookings sometimes carry premium charges.
Group cottage entertainment & activities
Stuff in the cottage itself - Look for properties with games rooms and pool tables. Houses to rent with hot tubs give you something to do without leaving the property. Some spacious holiday homes include cinema rooms and indoor pools which work brilliantly for families and big groups.
Coordinating group activities like a pro - Create a shared document where everyone can suggest activities. Don't try to keep the whole group together constantly. Split into smaller groups based on interests and energy levels.
Creating itineraries that please everyone - Build in downtime because not everyone wants to be busy constantly. Mix active days with relaxed ones. Leave some slots completely unplanned for spontaneous decisions.
Think about how far it is to activities or attractions - Check actual driving times to places you want to visit. Cheltenham Racecourse and Pittville Park are close to town centre properties. The Cotswolds attractions spread out more and need proper planning.
Backup plans for when the weather's rubbish - Book at least two indoor activities in advance. Cheltenham has excellent museums and shopping. Properties with indoor pools or games rooms become essential during wet weekends and Christmas breaks.
Some things to plan in advance
- Being too isolated with no shops or restaurants nearby means someone has to drive for every meal
- Parking inadequate for multiple cars causes daily reshuffling nightmares
- Who organizes everything including food shopping, activities and transport needs deciding before you arrive
- Who's responsible if something breaks should be clear from the rental agreement
- Managing different sleep schedules matters in properties where bedrooms share walls
Top 5 group attractions in Cheltenham
Cheltenham transformed from a market town into an elegant spa destination during the Regency period. The wide tree-lined streets and grand terraces still define the town centre today. For groups the mix of cultural venues and outdoor spaces works perfectly.
#1 Cheltenham Racecourse
The home of National Hunt racing hosts the famous Cheltenham Festival every March. The venue accommodates large groups brilliantly with various hospitality packages and viewing areas. Even if you're not racing fans the atmosphere during festival week is electric and the facilities handle crowds expertly.
#2 Pittville Park and Pump Room
This 57-acre park features lakes, playgrounds and the stunning Pump Room building where you can still taste the spa water. Groups love it because there's space for everyone to spread out. The park works for all ages from toddlers to grandparents making it ideal for family reunions.
#3 The Wilson Art Gallery and Museum
This Cheltenham institution combines art galleries with local history exhibits and the tourist information centre. Free entry makes it budget-friendly for big groups. The building itself is a beautiful example of Victorian architecture and the collections cover everything from fine art to archaeology.
#4 Holst Birthplace Museum
The composer Gustav Holst was born in this Regency terraced house. The museum recreates Victorian and Edwardian domestic life across multiple rooms. Groups can book guided tours and the compact size means you won't lose anyone during your visit.
#5 Cotswold Way Walking Trail
The northern terminus of this 102-mile National Trail sits right in Cheltenham. Groups can tackle short sections without committing to the full route. The nearby Cleeve Hill offers spectacular views across the Severn Vale and works brilliantly for mixed ability groups.
Indoor activities
| Attraction | What you'll experience | For groups |
|---|---|---|
| The Wilson Art Gallery and Museum | Art collections, local history exhibits and interactive displays across multiple galleries | Free entry and varied collections mean something for everyone regardless of interests |
| Holst Birthplace Museum | Period room settings showing Victorian and Edwardian life with personal items from the composer | Compact layout keeps groups together and guided tours available for parties |
| Everyman Theatre | Professional productions from drama to comedy in an intimate Edwardian playhouse | Group booking discounts available and varied programme suits different tastes |
| Cheltenham Town Hall | Concerts, comedy shows and events in a grand Victorian venue | Large capacity handles big groups easily with good facilities and central location |
| The Brewery Quarter | Shopping, restaurants, cinema and bars in converted Victorian brewery buildings | Everyone can split up and do their own thing then regroup for meals |
Visitor FAQs
How far in advance should we book Big Cottages in Cheltenham?
For popular dates like Christmas, New Year and the Cheltenham Festival in March, book 6-12 months ahead. Weekend breaks and hen party accommodation during summer need 3-6 months notice. Last minute availability exists but limits your choice significantly.
What size property do we need for our group?
Count actual guests not just bedrooms. A property that sleeps 14 might have several twin rooms. Check bed configurations carefully. For stag dos and hen parties consider if you need a 10 bedroom house or if cottages for 10 with flexible sleeping works better.
Are there properties suitable for one night stays?
Most large holiday rentals require minimum two or three night bookings especially for weekends. Some lodges and villas offer one night stays midweek. Expect to pay premium rates for short breaks.
What about properties with hot tubs for large groups?
Many spacious group accommodation options include hot tubs. Check capacity because a 6-person hot tub doesn't work well for groups of 12 or more. Properties with hot tubs often have higher cleaning fees.
Can we bring dogs to group cottages?
Plenty of dog friendly large cottages exist around Cheltenham. Most charge per pet and limit numbers to 2-3 dogs. Properties with enclosed gardens are essential if you're bringing multiple dogs. Always declare pets when booking.
Finding the right group cottage in Cheltenham sets up your entire break for success. We recommend using sites like Snaptrip to compare properties and read genuine reviews. The town gives you that perfect balance of things to do alongside proper downtime in your holiday home. Whether you're planning a family reunion, celebrating New Year or just gathering friends for a weekend, the combination of elegant town amenities and Cotswolds countryside makes Cheltenham work brilliantly for groups of all sizes.