Tolland Holiday Rentals from NZ$294: Search Short-Term Rentals

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Our top choices for Tolland holiday 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.

includes taxes & fees

2 Nov - 3 Nov

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.

includes taxes & fees

22 Oct - 23 Oct

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.

includes taxes & fees

23 Oct - 24 Oct

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

4. Peaceful Meadow Retreat

Granby

Todd R.

includes taxes & fees

26 Oct - 27 Oct

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.

includes taxes & fees

3 Nov - 4 Nov

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.

includes taxes & fees

28 Oct - 29 Oct

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.

includes taxes & fees

27 Oct - 28 Oct

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.

includes taxes & fees

16 Nov - 17 Nov

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.

includes taxes & fees

16 Nov - 17 Nov

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.

includes taxes & fees

25 Oct - 26 Oct

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

11. 1 Queen Bed | Micfridge

Windsor Locks

Anonymous traveller

includes taxes & fees

16 Nov - 17 Nov

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.

includes taxes & fees

26 Oct - 27 Oct

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 traveller

includes taxes & fees

2 Nov - 3 Nov

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.

includes taxes & fees

15 Nov - 16 Nov

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

includes taxes & fees

16 Nov - 17 Nov

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.

includes taxes & fees

16 Nov - 17 Nov

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

includes taxes & fees

2 Nov - 3 Nov

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.

includes taxes & fees

21 Oct - 22 Oct

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.

includes taxes & fees

20 Oct - 21 Oct

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.

includes taxes & fees

2 Nov - 3 Nov

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Top Tolland Hotel Reviews

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent

"!"

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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Tolland holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Tolland. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Tolland. Seeing all the best attractions is bound to make you fall in love with Tolland. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Tolland short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Tolland?

Yes, there are holiday rentals close to the most popular sights in Tolland, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Tolland has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of Tolland is located near skiing, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Tolland?

With 6 Expedia holiday rentals, you're guaranteed 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 wider area.

What’s a holiday rental in Tolland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Tolland. Holiday rentals offer extras such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for family trips or small group gatherings.

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Check prices for these dates

Our top choices for Tolland holiday 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 holiday rentals that suit your style

Top Tolland Hotel Reviews

Sheraton Hartford Hotel at Bradley Airport

La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

Red Roof Inn PLUS+ West Springfield

The Red Lion Inn

Hampton Inn West Springfield

Quality Inn Great Barrington

Holiday Inn Club Vacations Oak 'n Spruce Resort

Quality Inn West Springfield

Blue A Modern Hotel, an Ascend Collection Hotel

Find out more about Tolland

Frequently asked questions

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