Woodstock Valley Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Woodstock Valley vacation rentals

A wooden cabin with a balcony and stairs, surrounded by trees.

1. Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (37 reviews)
"Beautiful treehouse with everything you need. My kids loved picking blueberries and meeting the farm animals!"
United States
Lauren B.
$254 nightly
The price is $289
Nov 18 - Nov 19
Total with taxes and fees
Treehouse - Countryside - Farm Animals - Fire Pit
A group of people seated around a fire pit in a garden with a gazebo and trees in the background.

2. Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (24 reviews)
"The place was unique and cozy. The hosts were very friendly and our stay was great"
United States
Stacy
$230 nightly
The price is $261
Nov 22 - Nov 23
Total with taxes and fees
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
A modern interior with a dining area, kitchen, and seating space.

3. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Putnam
10.0 out of 10, Exceptional, (4 reviews)
"Offers good value with cozy accommodations."
United States
Anonymous traveler
$87 nightly
The price is $100
Nov 14 - Nov 15
Total with taxes and fees
1 King Bed | Non-Smoking, Micfridge
A two-story house with a front porch, stone steps, and a driveway.

4. Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
8.8 out of 10, Excellent, (9 reviews)
"Very convenient 2BD for a two night stay. Note that parking is on the street."
United States
Dan M.
$150 nightly
The price is $171
Nov 13 - Nov 14
Total with taxes and fees
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
A wooden deck with outdoor furniture, overlooking a lake with boats and houses in the background.

5. Serene 2-bedroom, 2-bath lakefront retreat on Staffordville Lake for 5 people.

Serene 2-bedroom, 2-bath lakefront retreat on Staffordville Lake for 5 people.
Stafford
9.6 out of 10, Exceptional, (50 reviews)
"Wonderful stay. Perfect spot on lake w kayaks already there very clean and had everything we needed!! We loved our stay and so relaxed."
United States
Lisa S.
Serene 2-bedroom, 2-bath lakefront retreat on Staffordville Lake for 5 people.
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

6. Modern 1-bedroom apartment in peaceful Sturbridge with AC

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
6.0 out of 10, (3 reviews)
"Clean place short drive to all Sturbridge attractions."
United States
Lynn M. T.
$111 nightly
The price is $124
Nov 15 - Nov 16
Total with taxes and fees
Modern 1-bedroom apartment in peaceful Sturbridge with AC
A house with a white porch, a black door, and a window with a white frame.

7. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
9.2 out of 10, Wonderful, (5 reviews)
"I had a lovely stay at the cottage! It was clean, comfortable, and quiet with a great view. The hosts were very helpful."
United States
Aaron H.
$232 nightly
The price is $264
Nov 15 - Nov 16
Total with taxes and fees
Cozy 1-bedroom cottage in serene Pomfret.
A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

8. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (46 reviews)
"Nice place to stay has good air conditioning "
United States
Zachary P.
$163 nightly
The price is $186
Nov 15 - Nov 16
Total with taxes and fees
The Tree House at Underhill Hollow
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

9. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 reviews)
"Great stay!!"
United States
Elizabeth G.
$158 nightly
The price is $180
Nov 15 - Nov 16
Total with taxes and fees
Wizard's Roost at Underhill Hollow
A wooden cabin with a glass upper floor, surrounded by a forest.

10. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (39 reviews)
"Excellent location for a quiet and relaxing getaway. The cabin was clean and well outfitted. Our host greeted us, talked about the history of the property, kayaking around the lake was great, such a good idea for an old youth camp with so much potential. We’ll definitely be returning for another stay"
United States
Zachary C.
$233 nightly
The price is $246
Nov 14 - Nov 15
Total with taxes and fees
Dove Cabin up in the Trees
A rustic building with a brick exterior and a red roof, situated next to a pond with tall reeds and a tree with autumn-colored leaves.

11. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (20 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
$159 nightly
The price is $181
Nov 16 - Nov 17
Total with taxes and fees
SteamPunk Bunk House and Intergalactic Way Station
A dining area with a high ceiling, skylights, and a view of the outdoors.

12. Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (95 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
$513 nightly
The price is $588
Nov 13 - Nov 14
Total with taxes and fees
Secluded 2-Acre Lakefront Home! Book Your Getaway!
A window with a view of a grassy field and trees.

13. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
10.0 out of 10, Exceptional, (11 reviews)
"I was looking for a place that was central to a couple of Renaissance Faires in the area and ended uo choosing this one due to its location and affordability. What an awesome place to stay. We're considering staying here next year when the Faires return."
United States
Kevan W.
$257 nightly
The price is $293
Nov 15 - Nov 16
Total with taxes and fees
Spacious, unique barn with beautiful views.
A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

14. Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Brimfield
9.2 out of 10, Wonderful, (12 reviews)
"What a beautiful set up for a pet friendly family stay - candles lit upon arrival and a child’s room filled with toys ready to be enjoyed."
United States
Gregory C.
$175 nightly
The price is $195
Nov 15 - Nov 16
Total with taxes and fees
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A bedroom with a wooden bed, large windows, and a view of greenery outside.

15. Rustic Farmette Studio with Hot Tub & Pool

Rustic Farmette Studio with Hot Tub & Pool
Thompson
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful and quiet location"
United States
Lynn J.
$323 nightly
The price is $368
Nov 13 - Nov 14
Total with taxes and fees
Rustic Farmette Studio with Hot Tub & Pool
A room with a wooden ceiling, a ceiling fan, a blue door, and a dining area with a table and chairs.

16. Lakefront - King - W&D - PetsOK - Kayaks - SUPs

Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (49 reviews)
"Nice location, just a short walk to the water."
United States
Harris G.
$262 nightly
The price is $299
Nov 18 - Nov 19
Total with taxes and fees
Lakefront - King - W&D - PetsOK - Kayaks - SUPs
A house with a stone chimney, a fire pit, and two Adirondack chairs in the yard.

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

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
8.8 out of 10, Excellent, (56 reviews)
"Wonderful lake house with a short walk to the beach! Our family of 5 had a wonderful, very relaxing time here."
United States
Blithen D.
$248 nightly
The price is $283
Dec 1 - Dec 2
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

18. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (4 reviews)
"Gorgeously decorated and ultra-clean. Was the perfect rental for my sisters wedding at Salem Cross Inn"
United States
Trish N.
$285 nightly
The price is $318
Dec 1 - Dec 2
Total with taxes and fees
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
A lakeside cabin with a deck, a dock, and a small docked boat.

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

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Sturbridge
9.8 out of 10, Exceptional, (98 reviews)
"very clean, wonderful location"
United States
Anonymous traveler
$427 nightly
The price is $477
Nov 16 - Nov 17
Total with taxes and fees
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
A cozy living room with a wooden dining table, a sofa, a ceiling fan, and a view of the outdoors through a window.

20. Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern

Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern
Coventry
8.8 out of 10, Excellent, (15 reviews)
"This is a quaint little town with a lot of neat places to visit"
United States
Edwin D.
$280 nightly
The price is $319
Nov 15 - Nov 16
Total with taxes and fees
Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern
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.
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Top Woodstock Valley Hotel Reviews

An outdoor patio area with seating, tables, and decorative lights.
Wellsworth Hotel

Wellsworth Hotel

Wellsworth Hotel
Southbridge

10/10 Excellent

what a GREAT find, we absolutely loved our stay here and would like to spend 3-4 days next time. We came in town for the Brimfield Antique and Flea Market Show and found this property. It was amazing - pool, hot tub, health club, Gym, Hand Ball / Racquetball, it really offers so much. Pool tables in the lounge area. The property is rich with history and it is beautiful.
United States
Brian
Reviewed September 7, 2024
Wellsworth Hotel

Find out more about Woodstock Valley

Everything you need to know about Woodstock Valley 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 Woodstock Valley 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 Woodstock Valley vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Woodstock Valley vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Woodstock Valley. 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 Woodstock Valley 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 $99 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 Woodstock Valley rentals

At Expedia, we put the best Woodstock Valley 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 Woodstock Valley 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 Woodstock Valley 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 Woodstock Valley. 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

Can I find vacation rentals in Woodstock Valley?

Yes, you can find vacation rentals close to well known local attractions in Woodstock Valley, or you can select a secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals that Woodstock Valley has to offer?

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8: This vacation home rental near Woodstock Valley is located in a rural location and has a garden, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What’s there to see and do in Woodstock Valley?

Explore the area and family-friendly sights such as Mohegan Bowl, or get out into nature at a spot like Crystal Pond. Crystal Pond Park and Campert Preserve are other places to visit while you're in town.

What’s a vacation rental in Woodstock Valley like?

Vacation rentals are private properties you can book for short or long periods in Woodstock Valley. Vacation rentals feature extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a family trip.