Woodstock Holiday Rentals

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Holiday Rentals in Woodstock

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Woodstock
9.8 out of 10, Exceptional, (75)
"Lovely stay on the lake, we enjoyed the location and the kayaks on the lake. "
United States
Lucy H.
The price is AU$762
includes taxes & fees
2 Dec - 3 Dec
Secluded 2-Acre Lakefront Home! Book Your Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!

Woodstock
10.0 out of 10, Exceptional, (20)
"We had a great stay at the lakehouse. Will definitely consider a future stay."
United States
Savanna
The price is AU$735
includes taxes & fees
2 Dec - 3 Dec
Stunning Lakefront Escape! Book Your Dream Getaway!

Treehouse - Countryside - Farm Animals - Fire Pit

Willington
9.4 out of 10, Exceptional, (28)
"My husband and I were exploring a number of birding hotspots in the quiet corner and decided to try the treehouse. We woke to the dawn bird chorus (without any ambient road noise). Just dreamy!"
United States
Jennifer H.
The price is AU$407
includes taxes & fees
9 Dec - 10 Dec
Treehouse - Countryside - Farm Animals - Fire Pit

Wizard's Roost at Underhill Hollow

North Grosvenordale
9.6 out of 10, Exceptional, (20)
"Full of whimsy, loved all of the details of the construction and decor. Great place to stay"
United States
Meghann H.
The price is AU$243
includes taxes & fees
2 Dec - 3 Dec
Wizard's Roost at Underhill Hollow

The Tree House at Underhill Hollow

Thompson
9.4 out of 10, Exceptional, (34)
"We had a magical stay! Hosts were accommodating to our needs and eager to make our visit the best."
United States
Grahame E.
The price is AU$267
includes taxes & fees
2 Dec - 3 Dec
The Tree House at Underhill Hollow

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

Sturbridge
9.8 out of 10, Exceptional, (89)
"Very Clean, great location"
United States
Anonymous traveller
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Charming 2-bedroom apartment in welcoming Putnam

Putnam
9.0 out of 10, Wonderful, (2)
"Very nice place. Quiet neighborhood and close to town. "
United States
michael C.
The price is AU$267
includes taxes & fees
2 Dec - 3 Dec
Charming 2-bedroom apartment in welcoming Putnam

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Stafford
9.8 out of 10, Exceptional, (29)
"FANTASTIC STAY! there was an issue after arrival that was QUICKLY addressed... rest of stay was amazing! Beautiful home. Great kayaks.. lots of fishing!QUICK AND PLEASANT COMMUNICATIONS.THANK YOU!!!"
United States
Michelle O.
The price is AU$482
includes taxes & fees
8 Dec - 9 Dec
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Bungalow 19 by the lake in Brimfield

2.0 star property
Brimfield
10.0 out of 10, Exceptional, (2)
"Clean, comfortable and great communication with host!"
United States
Elizabeth P.
Bungalow 19 by the lake in Brimfield

Spectacular waterfront cottage on the most beautiful lake in CT's 'Quiet Corner'

Killingly
10.0 out of 10, Exceptional, (50)
"Our Family enjoyed staying in your lake house. We had an amazing experience. It felt like home."
United States
Lisa G.
Spectacular waterfront cottage on the most beautiful lake in CT's 'Quiet Corner'

Leicester Lake Front Home, Come Relax!

Leicester
10.0 out of 10, Exceptional, (32)
"The home was lovely and the lakefront spot was beautiful! It was a very relaxing stay. "
United States
Erik S.
Leicester Lake Front Home, Come Relax!

4-bedroom house in Windham - Pet Friendly - Thread City Family Escape

Windham
9.8 out of 10, Exceptional, (8)
"Great house for family visit with our USCG cadet. The owners were very flexible and responsive to our needs. The property was clean and spacious we will use again! "
United States
Mark M.
The price is AU$809
includes taxes & fees
2 Dec - 3 Dec
4-bedroom house in Windham - Pet Friendly - Thread City Family Escape

The Lake House

Coventry Lake
9.8 out of 10, Exceptional, (20)
"Very nice place, we enjoyed our stay!"
United States
David G.
The Lake House

Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!

West Brookfield
10.0 out of 10, Exceptional, (15)
"The house was beautiful. Very clean, pet friendly, very good communication with owner."
United States
JUNE
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!

Cozy 2-Floor Apartment with Garage Access

Main South
9.8 out of 10, Exceptional, (27)
"Overall great place, parking in garage was great! "
United States
Michell M.
Cozy 2-Floor Apartment with Garage Access

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

Willington
9.6 out of 10, Exceptional, (11)
"Very educational and fun time on the farm"
United States
David S.
The price is AU$369
includes taxes & fees
8 Dec - 9 Dec
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing

Spacious 4-bedroom with four and half bathrooms

Worcester
10.0 out of 10, Exceptional, (5)
"We needed a place to stay while our hardwood floors were being refinished and this was perfect. We have a dog and 2 cats and there was plenty of space. The house was clean and as advertised."
United States
Deb H.
The price is AU$798
includes taxes & fees
2 Dec - 3 Dec
Spacious 4-bedroom with four and half bathrooms

SteamPunk Bunk House and Intergalactic Way Station

Thompson
10.0 out of 10, Exceptional, (14)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is AU$258
includes taxes & fees
2 Dec - 3 Dec
SteamPunk Bunk House and Intergalactic Way Station

Spacious Massachusetts Apartment #2

West Brookfield
9.0 out of 10, Wonderful, (29)
"We used both apartments for time with extended family. Nice to be in the same building."
United States
Tyler K.
The price is AU$463
includes taxes & fees
2 Dec - 3 Dec
Spacious Massachusetts Apartment #2

Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

Spencer
10.0 out of 10, Exceptional, (199)
"Great time spent with family"
Canada
Marianne B.
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
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 Hotel Reviews

Find out more about Woodstock

Everything you need to know about Woodstock holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Woodstock holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Woodstock holiday rentals: An excellent choice for every season

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

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Woodstock holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Woodstock holiday rentals we have selected for you start as low as AU$243 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Woodstock rentals

At Expedia, we put the best Woodstock holiday 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 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 holiday.

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. 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 a holiday rental in Woodstock?

Yes, there are holiday rentals close to the most popular sights in Woodstock, or you can select a more secluded option if you're looking for a relaxing stay. Woodstock is known for its festivals and wineries. Make sure you have time to check out the golf courses while you're in the area.

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!: This highly rated holiday home rental in Woodstock is located on a lake, and has a patio, a selection of games 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. Our travellers also rate Stunning Lakefront Escape! Book Your Dream Getaway! as a favourite home for rent in Woodstock.

How many holiday rentals are there in Woodstock?

Expedia has 8 holiday rentals for your stay in Woodstock.

What can I see and do in Woodstock?

Black Pond and Woodstock Town Beach are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Woodstock Golf Course and Taylor Brooke Winery.

What are holiday rentals like in Woodstock?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Woodstock. Holiday rentals feature extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for families.