Tolland Vacation Rentals from $165: Search Short-Term Rentals

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Our top choices for Tolland vacation rentals

A recreational vehicle with a beige sofa, pillows, a small table, and potted plants.

1. Cozy Camper tucked into the woods

Sandisfield

"This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably...

hannah w.

$179 nightly

Nov 10 - Nov 11

Total with taxes and fees

A house with a porch, a garden with pink flowers, and a stone wall along the road.

2. Big farmhouse in the foothills of the Berkshires

Russell

Dale B.

$340 nightly

Oct 22 - Oct 23

Total with taxes and fees

A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

3. Cozy Cottage-Sunset On The Lake

Otis

Michael S.

$521 nightly

Oct 23 - Oct 24

Total with taxes and fees

A square fire pit with flames, surrounded by a grassy field and a green chair.

4. Peaceful Meadow Retreat

Granby

Todd R.

$164 nightly

Oct 26 - Oct 27

Total with taxes and fees

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Sherwood Forest

William C B.

$284 nightly

Nov 3 - Nov 4

Total with taxes and fees

A hot tub with a string of lights above it, set against a dark night sky.

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

Sherwood Forest

Frank M.

$352 nightly

Oct 28 - Oct 29

Total with taxes and fees

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

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

Sherwood Forest

Sharon K.

$336 nightly

Oct 27 - Oct 28

Total with taxes and fees

A wooden cabin interior with a bench, a rug, and a hanging plant.

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

Winchester

Thomas C.

$186 nightly

Nov 1 - Nov 2

Total with taxes and fees

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

9. 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.

$533 nightly

Nov 9 - Nov 10

Total with taxes and fees

A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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

Great Barrington

Deborah S.

$148 nightly

Oct 25 - Oct 26

Total with taxes and fees

A hotel room with a bed, a nightstand, a lamp, and a wardrobe.

11. 1 Queen Bed | Micfridge

Windsor Locks

Anonymous traveler

$78 nightly

Nov 5 - Nov 6

Total with taxes and fees

A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

12. Sun Filled Lake House Living

Avon

Joseph C.

$246 nightly

Oct 26 - Oct 27

Total with taxes and fees

A hotel lobby with a reception desk, a seating area with chairs and a table, and a large window providing natural light.

13. 1 Queen Bed | ADA/Tub/Micfridge

Windsor Locks

Anonymous traveler

$78 nightly

Nov 5 - Nov 6

Total with taxes and fees

A balcony with a view of a lake, white railings, and outdoor furniture.

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

Collinsville

Mary S.

$297 nightly

Oct 25 - Oct 26

Total with taxes and fees

A cozy room with two beds, large windows, and a view of a snowy landscape.

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

Easthampton Ma.

Paula

$248 nightly

Nov 2 - Nov 3

Total with taxes and fees

A two-story house with a front porch, a small balcony, and a white picket fence.

16. Cozy Attic 10 min to Llitchfield

Torrington

Nicole N.

$313 nightly

Nov 3 - Nov 4

Total with taxes and fees

A modern kitchen with blue cabinets, a dining area with a glass table, and a living room with a brown leather sofa.

17. Collinsville River Escape / Fall Foliage, Deck & Yard

Collinsville

"We loved the place, which feels like your own house in the woods. The setting is gorgeous especially with the leaves changing colors. We specifically chose the location so we could bike the Farmington Trail loop which starts at the bottom of the hill. The house is so well stocked with everything you could think of, especially coffee and there is plenty of space to relax inside and out. The host was very attentive to our needs. It couldn’t have been better for us."

Margaret A.

$197 nightly

Nov 9 - Nov 10

Total with taxes and fees

A modern kitchen with a marble island, bar stools, a stainless steel stove, and a decorative chandelier.

18. Cozy 2-bedroom apartment with movie theater.

Agawam

London R.

$312 nightly

Oct 19 - Oct 20

Total with taxes and fees

A red door with a wicker basket hanging on it, leading to a laundry area with a brick wall and two large speakers.

19. The Historic Hideaway

Avon

Nicole M.

$252 nightly

Oct 20 - Oct 21

Total with taxes and fees

A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

20. Art House 3 Beds Close to Warner Theater

Torrington

Brittany M.

$376 nightly

Nov 2 - Nov 3

Total with taxes and fees

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Top Tolland Hotel Reviews

La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

8/10 Good

"Plenty of parking. Bathroom fan made a lot of noise when light was turned on and internet was almost nonexistent."

Hampton Inn West Springfield

8/10 Good

"Room was clean, microwave and refrigerator clean and working, staff was friendly and helpful. Breakfast was better than most. The bath however had problems. The water faucet was loose and not connected to the tub and the water control was difficult to pull to start. Tub plug was very hard to use."

Quality Inn West Springfield

10/10 Excellent

"Overall I had a great two day stay at the Quality Inn. I have stayed here over a dozen times when in the area to visit Six Flags, my previous visit was in the spring, and they have made some updates since! I noticed new chairs in the hallways and room, and the exterior of the building was repainted a new color and looks more modern! I had room 421, a 2 queen, which was mostly clean and comfortable. Only issue was the new tan chair by the door looked comfortable, but I did not sit in it, as it had long hairs and sticky residue all over the cushion... Otherwise the room was clean, beds were comfortable with 4 pillows on each bed, lots of towels, and fridge worked great! The lamp between the bed did not work though... At check in, the man with tattoos on his hands wasn't that friendly or welcoming but did honor my request for a higher floor. Later, when returning from dinner next door (Great Japanese restaurant!) I heard him tell a guest she had the entire 5th floor to herself, which was annoying as each night I had neighbors who I could hear easily through the walls... Why not space out guests when there is space? I woke up my first morning to hearing the neighbors talk... Breakfast was fine with a decent variety, I liked the donuts, eggs were decent, as was the sausage. The room was a great value and I will return. It looks like the first floor was restored for guest use again too! Nice to see some changes and hope they continue renovating and updating the property!"

Blue A Modern Hotel, an Ascend Collection Hotel

10/10 Excellent

"We had a wonderful stay! The staff were incredibly friendly and welcoming. Everything in the hotel is beautiful, modern, fresh and brand new. We were especially impressed by the complimentary massage chairs in the room. Highly recommend this hotel!"

Find out more about Tolland

Everything you need to know about Tolland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Tolland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Tolland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Tolland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Tolland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Tolland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $165 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Tolland rentals

At Expedia, we put the best Tolland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Tolland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Tolland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Tolland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental outside of Tolland is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and 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. Maple Corner Farm Cross Country Ski Area and Hartland Recreation Area 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. Cozy Camper tucked into the woods

2. Big farmhouse in the foothills of the Berkshires

3. Cozy Cottage-Sunset On The Lake

4. Peaceful Meadow Retreat

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

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

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

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

9. Treetop Hideaway in Tyringham

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

11. 1 Queen Bed | Micfridge

12. Sun Filled Lake House Living

13. 1 Queen Bed | ADA/Tub/Micfridge

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

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

16. Cozy Attic 10 min to Llitchfield

17. Collinsville River Escape / Fall Foliage, Deck & Yard

18. Cozy 2-bedroom apartment with movie theater.

19. The Historic Hideaway

20. Art House 3 Beds Close to Warner Theater

Find vacation rentals that suit your style

Top Tolland Hotel Reviews

La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

Hampton Inn West Springfield

Quality Inn Great Barrington

Holiday Inn Club Vacations Oak 'n Spruce Resort

Quality Inn West Springfield

Sheraton Hartford Hotel at Bradley Airport

Blue A Modern Hotel, an Ascend Collection Hotel

Riverdale Inn

Find out more about Tolland

Frequently asked questions

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