Tolland Vacation Rentals from ￥50,109: Search Short-Term Rentals

Q: What's the top vacation rental that Tolland has to offer?

Cozy Riverside Berkshires Retreat : This vacation home rental outside of Tolland is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and kitchenware, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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Our top choices for Tolland vacation rentals

1. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

winsted

Steve

￥38,405 total

includes taxes & fees

Sep 1 - Sep 2

2. Big farmhouse in the foothills of the Berkshires

Russell

Will G.

￥56,598 total

includes taxes & fees

Sep 7 - Sep 8

3. Peaceful Meadow Retreat

Granby

Todd R.

￥29,663 total

includes taxes & fees

Sep 10 - Sep 11

4. Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

William C B.

￥48,061 total

includes taxes & fees

Sep 13 - Sep 14

5. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

Frank M.

￥63,227 total

includes taxes & fees

Sep 7 - Sep 8

6. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Sharon K.

￥60,629 total

includes taxes & fees

Sep 9 - Sep 10

7. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

Otis

￥54,933 total

includes taxes & fees

Sep 15 - Sep 16

8. Linny's - Private Dock - Lake Access - Firepit

West Suffield

Wendy C.

￥64,020 total

includes taxes & fees

Sep 13 - Sep 14

Coffee/tea maker, fridge, microwave, oven

9. Cozy 1-bedroom studio in serene Great Barrington with AC

Great Barrington

bob i.

￥26,256 total

includes taxes & fees

Sep 7 - Sep 8

10. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Winchester

￥35,750 total

includes taxes & fees

Aug 30 - Aug 31

11. River Overlook - What a view from your deck!

Collinsville

Mary S.

￥51,629 total

includes taxes & fees

Sep 8 - Sep 9

12. Cozy Modern Farmhouse Private Apt - 3 Beds

Torrington

Louisa A.

￥54,690 total

includes taxes & fees

Aug 30 - Aug 31

Desk, iron/ironing board, travel crib, WiFi

13. The Creation Station is a cozy place so make yourself at home.

Easthampton Ma.

Paula

￥44,857 total

includes taxes & fees

Aug 31 - Sep 1

14. Cozy 2-bedroom apartment with movie theater.

Agawam

London R.

￥49,962 total

includes taxes & fees

Aug 31 - Sep 1

15. Cozy Attic 10 min to Llitchfield

Torrington

Nicole N.

￥43,512 total

includes taxes & fees

Aug 30 - Aug 31

16. Pristine Cozy Walkable Downtown 2BR Getaway

Torrington

James M.

￥44,545 total

includes taxes & fees

Aug 31 - Sep 1

17. Art House 3 Beds Close to Warner Theater

Torrington

Brittany M.

￥69,190 total

includes taxes & fees

Sep 1 - Sep 2

18. Treetop Hideaway in Tyringham

Monterey

"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "

Samantha G.

￥93,236 total

includes taxes & fees

Sep 21 - Sep 22

19. Cozy Riverside Berkshires Retreat

Great Barrington

Colin E.

￥50,109 total

includes taxes & fees

Sep 8 - Sep 9

20. Sun Filled Lake House Living

Avon

Joseph C.

￥48,072 total

includes taxes & fees

Sep 9 - Sep 10

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Top Tolland Hotel Reviews

Holiday Inn Express & Suites Bradley Airport by IHG

10/10 Excellent

"I especially like that the hallway and room were not carpeted. No icky carpets. The room has lots of charging stations which is great. They provide easy to carry breakfast items like banana, yogurt and muffins for those leaving on super early flights."

The Red Lion Inn

10/10 Excellent

"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"I am not a person who usually writes a review but I loved the place. Room was great. Staff was great. I had never been to an Indian restaurant but everywhere I went people raved about I so we went and it was wonderful. Only a few small issues. The fan in our bathroom room needs attention. Very loud. Something is failing. The wifi was very weak in my room. Kept cutting out. and just one other suggestion. The balcony on the upper level should have privacy screens on the sides. Other wise I would absolutely go back."

Candlewood Suites West Springfield by IHG

8/10 Good

"Staff extremely helpful and pleasant. Loved the room. Comfy beds. Loved having the kitchenette. The pool was nice; the jacuzzi was colder than the pool. But pool was a lovely temp. The only downside was we could hear then people walking above us at like 3 am. Walls and ceilings may be a tad thin. However, very pleasant experience. Very reasonable price and was perfect for our stay to be near Six Flags."

Find out more about Tolland

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Frequently asked questions

Are there vacation rentals in Tolland?

Yes, you can find vacation rentals close to top local attractions in Tolland, or you can select a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental that Tolland has to offer?

Cozy Riverside Berkshires Retreat: This vacation home rental outside of Tolland is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and kitchenware, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Tolland?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Tolland stay.

What’s there to see and do in Tolland?

While exploring the area, visit family-friendly sights like Flamig Farm, or get outside and enjoy nature at Otis Reservoir. Tolland State Forest and Hartland Town Hall are a couple of places you'll find in the larger area.

What’s a vacation rental in Tolland like?

Vacation rentals are privately owned properties you can book for a couple of days or more in Tolland. Vacation rentals offer extras like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for families.

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Check prices for these dates

Our top choices for Tolland vacation rentals

1. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

2. Big farmhouse in the foothills of the Berkshires

3. Peaceful Meadow Retreat

4. Real Estate: Therapy - Lake, Laundry, Love it

5. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

6. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

7. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

8. Linny's - Private Dock - Lake Access - Firepit

9. Cozy 1-bedroom studio in serene Great Barrington with AC

10. Peaceful and cozy 1 bed 1 bath in quaint Winchester

11. River Overlook - What a view from your deck!

12. Cozy Modern Farmhouse Private Apt - 3 Beds

13. The Creation Station is a cozy place so make yourself at home.

14. Cozy 2-bedroom apartment with movie theater.

15. Cozy Attic 10 min to Llitchfield

16. Pristine Cozy Walkable Downtown 2BR Getaway

17. Art House 3 Beds Close to Warner Theater

18. Treetop Hideaway in Tyringham

19. Cozy Riverside Berkshires Retreat

20. Sun Filled Lake House Living

Find vacation rentals that suit your style

Top Tolland Hotel Reviews

Holiday Inn Express & Suites Bradley Airport by IHG

Holiday Inn Club Vacations Oak 'n Spruce Resort

DoubleTree by Hilton Hartford - Bradley Airport

The Red Lion Inn

Candlewood Suites Windsor Locks Bradley Arpt by IHG

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

Springhill Suites Marriott Airport

Candlewood Suites West Springfield by IHG

Find out more about Tolland

Frequently asked questions

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