Book Holiday Homes in Tolland

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Tolland

Island Vibes Home

Island Vibes Home

Windsor
With a stay at this vacation home in Windsor, you'll be within a 10-minute drive of XL Center and Farmington River.
Island Vibes Home
15mins to Hartford, Home in Manchester w/ King Bed

15mins to Hartford, Home in Manchester w/ King Bed

2 out of 5
Manchester
With a stay at this vacation home in Manchester, you'll be within a 15-minute drive of XL Center and Rockville General Hospital.
15mins to Hartford, Home in Manchester w/ King Bed
Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!

Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!

Woodstock
The price is AU$822 per night from 2 Jan to 3 Jan
AU$822
includes taxes & fees
2 Jan - 3 Jan 2025
Located in Woodstock, this vacation home is on the waterfront, within a 10-minute drive of Bigelow Hollow State Park and Bishop Preserve.
Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!
Save an average of 15% on thousands of hotels when you're signed in
Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway!

Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway!

Woodstock
The price is AU$822 per night from 2 Jan to 3 Jan
AU$822
includes taxes & fees
2 Jan - 3 Jan 2025
When you stay at this vacation home in Woodstock, you'll be on the beach, within a 5-minute drive of Taylor Brooke Winery and Roseland Cottage.
Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway!
Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!

Sturbridge
The price is AU$1,528 per night from 26 Dec to 27 Dec
AU$1,528
includes taxes & fees
26 Dec - 27 Dec
When you stay at this vacation home in Sturbridge, you'll be on the waterfront, within a 5-minute drive of Old Sturbridge Village and St. Anne's Shrine.
Lake House in Sturbridge w/All the Views!
Beautiful 3BR, Rare Find, Clean & Guest Favorite

Beautiful 3BR, Rare Find, Clean & Guest Favorite

2 out of 5
West Hartford
The price is AU$481 per night from 20 Jan to 21 Jan
AU$481
includes taxes & fees
20 Jan - 21 Jan 2025
With a stay at this vacation home in West Hartford, you'll be within a 10-minute drive of XL Center and VA Newington.
Beautiful 3BR, Rare Find, Clean & Guest Favorite
PICON COZY

PICON COZY

Springfield
The price is AU$275 per night from 1 Jan to 2 Jan
AU$275
includes taxes & fees
1 Jan - 2 Jan 2025
With a stay at this vacation home in Springfield (Sixteen Acres), you'll be within a 10-minute drive of MGM Springfield and Vibra Hospital.
PICON COZY
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

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

Windsor
With a stay at this vacation home in Windsor, you'll be within a 10-minute drive of XL Center and Farmington River.
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
A “Wow” Experience everywhere there is something to stimulate your mind Interest

A “Wow” Experience everywhere there is something to stimulate your mind Interest

Windsor
The price is AU$1,109 per night from 28 Dec to 29 Dec
AU$1,109
includes taxes & fees
28 Dec - 29 Dec
With a stay at this vacation home in Windsor, you'll be within a 10-minute drive of XL Center and Wintonbury Hills Playground.
A “Wow” Experience everywhere there is something to stimulate your mind Interest
Don't see what you're looking for?
See all available properties in Tolland
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Tolland Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Tolland vacation homes are the perfect way for you to wing it.

Holiday houses in Tolland let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Tolland in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Tolland adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Tolland with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Tolland vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Tolland Holiday Homes essential information

Accommodation
133 Holiday Homes
Lowest Price
AU$156
Highest Price
AU$1,528
Popular accommodation
Island Vibes Home, 15mins to Hartford, Home in Manchester w/ King Bed, Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!, Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway!, Lake House in Sturbridge w/All the Views!, Beautiful 3BR, Rare Find, Clean & Guest Favorite, PICON COZY, NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!, A “Wow” Experience everywhere there is something to stimulate your mind Interest

Top trending hotels in Tolland

MGM Springfield

MGM Springfield

4 out of 5
One MGM Way, Springfield, MA
The price is AU$289 per night from 29 Dec to 30 Dec
AU$289
includes taxes & fees
29 Dec - 30 Dec
With a stay at MGM Springfield, you'll be centrally located in Springfield, within a 10-minute walk of MassMutual Center and Naismith Memorial Basketball Hall ...
MGM Springfield
The Capitol Hotel, Ascend Hotel Collection

The Capitol Hotel, Ascend Hotel Collection

3 out of 5
440 Asylum St, Hartford, CT
Fully refundable
The price is AU$156 per night from 5 Jan to 6 Jan
AU$156
includes taxes & fees
5 Jan - 6 Jan 2025
The Capitol Hotel, Ascend Hotel Collection is in the heart of Hartford, within a 5-minute walk of Bushnell Park and XL Center.
The Capitol Hotel, Ascend Hotel Collection
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St, Southbridge, MA
Fully refundableReserve now, pay when you stay
The price is AU$183 per night from 24 Dec to 25 Dec
AU$183
includes taxes & fees
24 Dec - 25 Dec
With a stay at Wellsworth Hotel, you'll be centrally located in Southbridge, within a 10-minute drive of Old Sturbridge Village and Southbridge Town Common.
Wellsworth Hotel
Save an average of 15% on thousands of hotels when you're signed in
Best Western Hartford Hotel & Suites

Best Western Hartford Hotel & Suites

2.5 out of 5
185 Brainard Rd, Hartford, CT
Fully refundableReserve now, pay when you stay
The price is AU$186 per night from 29 Dec to 30 Dec
AU$186
includes taxes & fees
29 Dec - 30 Dec
With a stay at Best Western Hartford Hotel & Suites, you'll be centrally located in Hartford, within a 5-minute drive of XL Center and Colt Park.
Best Western Hartford Hotel & Suites
Don't see what you're looking for?
See all available properties in Tolland
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.