Photo by Jim Stamatopoulos

Tolland County holiday lettings

We found holiday rentals — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

April 2025

May 2025

Discover a selection of 28 homes, 11 apartments and other holiday rentals in Tolland County that are perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, such as parking and air conditioning. No matter what you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Popular cities in Tolland County

Holiday rentals with weekly discounts - Tolland County

Showing deals for:25 Jul - 1 Aug

Exceptional

(9 reviews)

6mi to UConn; Peaceful Country Family Home

Ashford, CT

7% off

£149 per night

includes taxes & fees

Exceptional

(22 reviews)

Beautiful Lakefront Home in Heart of Massachusetts Near Antiquing and Breweries

Sturbridge, MA

8% off

£359 per night

includes taxes & fees

Exceptional

(13 reviews)

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

East Hampton, CT

8% off

£271 per night

includes taxes & fees

[Living Room, Downstairs] Sit back and watch the flames dance in the firepit while enjoying the water views.

Exceptional

(21 reviews)

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Coventry, Connecticut

16% off

£341 per night

includes taxes & fees

Exceptional

(52 reviews)

Beautiful Colonial Home in a Peaceful Setting Bordering Natchaug State Forest

Pomfret, CT

7% off

£369 per night

includes taxes & fees

Historic 1853 two-family home on 6 acres

Exceptional

(12 reviews)

Country getaway in 2 family home, huge yard & grounds, minutes from lakes & more

East Hampton, CT

8% off

£265 per night

includes taxes & fees

[Lake House] A Vibrant Retreat: Classic New England Lake Cottage with a Dog Run in the Rear.

Wonderful

(40 reviews)

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Coventry, Connecticut

16% off

£310 per night

includes taxes & fees

Exceptional

(15 reviews)

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

Windsor, CT

7% off

£130 per night

includes taxes & fees

Beautiful picture from the dock shows all the new stone work, patio & Firepit

Exceptional

(84 reviews)

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Sturbridge, MA

8% off

£628 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Tolland County

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Sleeps 8 · 2 bedrooms · 2 bathrooms

Top rated rentals - Tolland County

Premier Host

Bungalow at Eagleville

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Frequently asked questions

What is the best area to stay in Tolland County when booking a holiday rental?

If you’re considering a getaway to Tolland County, Coventry is one of the most popular locations to stay. Whether you want a cottage, condo or another property type, you’ll always have the whole place to yourself.

What is the most popular type of holiday rental accommodation in Tolland County?

The most desirable types of holiday rentals in Tolland County are houses. Ready for more choices? Vrbo offers a variety of options to match the diverse needs of our guests, so you’ll see properties in loads of shapes and sizes. The perfect fit is waiting for you — book yours today.

How much does it cost to rent a holiday rental in Tolland County?

The average price for a holiday rental in Tolland County can vary depending on factors like property type, length of stay and season. Whether you’re looking for a sprawling villa with lots of bedrooms or a quaint cottage just enough for two, just enter your dates of travel to view stays with fantastic value.

How much does it cost to rent a beach house in Tolland County?

The average price for a holiday rental close to the beach in Tolland County will depend on when you’re going and the type and size of property you’re searching for. Find prices easily and quickly on Vrbo by entering your dates of travel. Then use the filters to pick the number of bedrooms and amenities that you prefer, such as air conditioning, WiFi and a pool.

What are popular rental amenities in Tolland County?

A stovetop, a microwave oven and a fridge are the most popular rental amenities in Tolland County. Whether you’re taking a trip solo, with your sweetheart or a group of friends, Vrbo can help you find a holiday rental that fits your tastes with a load of extras you’ll love.

Are there large group holiday rentals in Tolland County?

With eight holiday rentals that can sleep 10 or more guests in Tolland County, you won’t have to hold back on your invites. From fun family get-togethers to special events like Thanksgiving or Christmas parties, Vrbo can help you find a large group rental to match the occasion.

What are the top attractions for families in Tolland County?

There are plenty of amazing things to see and do with the family in Tolland County, such as:

Stafford Motor Speedway
Crystal Lake Sandy Beach
Mansfield Drive-In Theatre

Can I find two-bedroom holiday rentals in Tolland County?

Gather your besties and enjoy total privacy and comfort in one of the eight two-bedroom holiday properties Tolland County has to offer.

Are there holiday rentals with WiFi in Tolland County?

Whether you’d like to stay in touch with world events, check emails or post a pic to social media, there are 12 holiday homes with WiFi in Tolland County. Check the “WiFi” box when searching on Vrbo and stay connected on your holiday.

How old do you have to be to rent a holiday rental in Tolland County?

The minimum required age is usually 16, 18 or 21. It can change across properties on Vrbo, so look at the rules of your chosen Tolland County stay before booking your stay.

How long can I rent a holiday rental in Tolland County for?

The amount of time you can book a Tolland County holiday home for differs depending on the property. Simply tap in your preferred travel dates to view available options that offer long-term stays. They have all you need to make your extended trip more comfortable and enjoyable, such as kitchens and yards. Some Vrbo holiday properties may also offer weekly or monthly discounts, so you can stay longer for less money.