Woodstock Valley Holiday Rentals

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Our top choices for Woodstock Valley holiday rentals

9.6 out of 10, Exceptional, (30)
"Great host- fun property!"
United States
Mary F.
The price is AU$389
includes taxes & fees
4 Jan - 5 Jan 2026
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
9.4 out of 10, Exceptional, (10)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
United States
Edward L.
The price is AU$511
includes taxes & fees
1 Jan - 2 Jan 2026
Trainmaster's Inn - Caboose
9.4 out of 10, Exceptional, (3)
"Very nice place. Quiet neighborhood and close to town. "
United States
michael C.
The price is AU$256
includes taxes & fees
6 Jan - 7 Jan 2026
Charming 2-bedroom apartment in welcoming Putnam
8.8 out of 10, Excellent, (48)
"It was great! Thank you :-) "
United States
Becki S.
The price is AU$422
includes taxes & fees
5 Jan - 6 Jan 2026
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
9.4 out of 10, Exceptional, (29)
"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$399
includes taxes & fees
7 Jan - 8 Jan 2026
Treehouse - Countryside - Farm Animals - Fire Pit
9.6 out of 10, Exceptional, (14)
"Very nice country stay. "
United States
michael C.
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
9.8 out of 10, Exceptional, (35)
"We were in town for a family event and the cottage was a perfect choice!Very comfortable, well appointed and just steps from the lake!I'll definitely book again next time I'm in town!"
United States
George J.
The price is AU$480
includes taxes & fees
4 Jan - 5 Jan 2026
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
9.4 out of 10, Exceptional, (39)
"Pet and family, friendly"
United States
Mary-Kate G
The price is AU$494
includes taxes & fees
12 Jan - 13 Jan 2026
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Apartment in West Brookfield

Apartment in town center #1
8.8 out of 10, Excellent, (26)
"Clean place and was well suited for what we needed"
United States
Chris
The price is AU$453
includes taxes & fees
11 Jan - 12 Jan 2026
Apartment in town center #1
10.0 out of 10, Exceptional, (14)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is AU$284
includes taxes & fees
1 Jan - 2 Jan 2026
SteamPunk Bunk House and Intergalactic Way Station
10.0 out of 10, Exceptional, (30)
"We had a very nice stay while there."
United States
Ann R.
The price is AU$272
includes taxes & fees
29 Jan - 30 Jan 2026
The Carriage House at Chaprae Hall
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$800
includes taxes & fees
4 Jan - 5 Jan 2026
4-bedroom house in Windham - Pet Friendly - Thread City Family Escape

Apartment in West Brookfield

Spacious Massachusetts Apartment #2
9.0 out of 10, Wonderful, (29)
"Really a cute place to stay, very clean and comfortable "
United States
Michelle J.
The price is AU$453
includes taxes & fees
11 Jan - 12 Jan 2026
Spacious Massachusetts Apartment #2
10.0 out of 10, Exceptional, (3)
"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.
The price is AU$399
includes taxes & fees
3 Jan - 4 Jan 2026
Spacious, unique barn with beautiful views.
9.4 out of 10, Exceptional, (20)
"Beautiful location. Great communication with host who continually checked in with us. Home had everything we needed to host my daughter and her friends for a great dinner for UCONN family weekend. Will definitely be back! "
United States
Michelle L.
The price is AU$460
includes taxes & fees
8 Jan - 9 Jan 2026
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
9.0 out of 10, Wonderful, (26)
"Loved the views of the lake and the decor. "
United States
Beth L.
The price is AU$478
includes taxes & fees
8 Jan - 9 Jan 2026
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
The price is AU$270
includes taxes & fees
12 Jan - 13 Jan 2026
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
10.0 out of 10, Exceptional, (1)
"Perfect quiet place to work and rest"
United States
michael C.
The price is AU$627
includes taxes & fees
7 Jan - 8 Jan 2026
Charming 1-bedroom apartment with AC, WiFi in pleasant Webster
2.0 star property
The price is AU$419
includes taxes & fees
1 Jan - 2 Jan 2026
Cozy 1-bedroom cottage in serene Pomfret.
The price is AU$368
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy apartment in quiet setting that is very convenient to UConn and ECSU.
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

Find out more about Woodstock Valley

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

Woodstock Valley holiday 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 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 Valley 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 Valley holiday rentals we have selected for you start as low as AU$284 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Woodstock Valley rentals

At Expedia, we put the best Woodstock Valley 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 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 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 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 holiday rentals in Woodstock Valley?

Yes, there are holiday rentals close to the most popular sights in Woodstock Valley, 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 Woodstock Valley has to offer?

Secluded 2-Acre Lakefront Home! Book Your Getaway!: This holiday home rental outside of Woodstock Valley 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.

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

Explore the area and family-friendly sights such as Martha's Herbary, 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 holiday rental in Woodstock Valley like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Woodstock Valley. Holiday rentals offer extras like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for a small group gathering.