Woodstock Holiday Rentals

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Holiday Rentals in Woodstock

Secluded 2-Acre Lakefront Home! Book Your Retreat!

9.8 out of 10, Exceptional, (66)
"The property was in great shape. Everything was as hoped for."
Secluded 2-Acre Lakefront Home! Book Your Retreat!

Charming country studio apartment in idyllic Woodstock - Woodstock Red Barn

10.0 out of 10, Exceptional, (6)
"Excellent place to stay to relax. Quiet and well appointed. "
Charming country studio apartment in idyllic Woodstock - Woodstock Red Barn

The Tree House at Underhill Hollow

9.6 out of 10, Exceptional, (21)
"Loved the treasure hunt and fairy gardens. "
The price is AU$268
includes taxes & fees
14 July - 15 July
The Tree House at Underhill Hollow

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

9.8 out of 10, Exceptional, (23)
"This property had easy access to the lake and had nice character. it was a quick overnight and wished we had more time to enjoy it. Kitchen pots and pans and bath towels could be updated. Bathroom door needs attention as its hard to close."
The price is AU$658
includes taxes & fees
21 July - 22 July
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Amazing lake house with everything you need!

10.0 out of 10, Exceptional, (14)
"Look ing forward to booking again. Summer would be great to use the lake.Brad was very nice and easy to get ahold of. Loved this place!!!!"
Amazing lake house with everything you need!

Treehouse - Countryside - Farm Animals - Fire Pit

9.8 out of 10, Exceptional, (26)
"Safe, inviting stay."
The price is AU$574
includes taxes & fees
5 Aug - 6 Aug
Treehouse - Countryside - Farm Animals - Fire Pit

Dove Cabin up in the Trees

10.0 out of 10, Exceptional, (14)
"This is the sweetest property to stay in when visiting Brimfield market. I highly suggest any of the cabins on the property "
The price is AU$401
includes taxes & fees
14 July - 15 July
Dove Cabin up in the Trees

Charming 2-bedroom cottage on 7 acres of woods in Putnam with AC, WiFi

Charming 2-bedroom cottage on 7 acres of woods in Putnam with AC, WiFi

Wizard's Roost at Underhill Hollow

10.0 out of 10, Exceptional, (13)
"Great host and amenities!"
The price is AU$262
includes taxes & fees
27 July - 28 July
Wizard's Roost at Underhill Hollow

Spacious 4-bedroom house in wonderful Worcester Area

10.0 out of 10, Exceptional, (1)
"We had room for each of the adults, which included adult children. At these ages they no longer want to share a bed or bathroom with anyone. Perfect that we could come together, but have our own separate spaces. Very clean and comfortable with everything you need."
The price is AU$789
includes taxes & fees
21 July - 22 July
Spacious 4-bedroom house in wonderful Worcester Area

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

9.8 out of 10, Exceptional, (13)
"Just a nice lake house!!"
The price is AU$536
includes taxes & fees
31 July - 1 Aug
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Lakefront Connecticut Retreat Near UConn

10.0 out of 10, Exceptional, (20)
"The house is beautiful and had everything we needed for the weekend. Since it was cooler and a bit rainy we only availed ourselves to the outside table for peaceful and quiet times. Our NYC family really enjoyed the quiet! We will be looking at this house in our future visits. "
Lakefront Connecticut Retreat Near UConn

Brand new 3 bedroom house in welcoming Worcester with WiFi and AC

10.0 out of 10, Exceptional, (1)
"New house with all of the accommodations! Kitchen is well fortified with new cookware and all of the essentials. Spacious, clean and inviting. Comfortable linens. Good communication and helpful throughout the stay. This Vrbo was well thought out! Kudos to the host!"
Brand new 3 bedroom house in welcoming Worcester with WiFi and AC

Luxury Home, Pool, fireplace

10.0 out of 10, Exceptional, (27)
"The property allowed for my extended family to gather under one roof and spend quality time together in a beautiful and quaint setting. "
Luxury Home, Pool, fireplace

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

9.0 out of 10, Wonderful, (21)
"We had such a wonderful time during our winter stay! The place was super cozy, and the heating made it feel like a warm retreat from the cold outside. We really appreciated the hospitality and can't wait to come back again! "
The price is AU$632
includes taxes & fees
21 July - 22 July
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

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

10.0 out of 10, Exceptional, (187)
"This was our third time staying, and definately won’t be our last!"
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

Quiet oasis in the city

The price is AU$1,421
includes taxes & fees
22 July - 23 July
Quiet oasis in the city

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

9.0 out of 10, Wonderful, (42)
"Perfect for everything we needed. Cute and cozy, and 12 miles from our son’s home. Our granddaughter stayed over one of the nights and loved having her own space (she is 4). We Will definitely stay again. "
The price is AU$618
includes taxes & fees
5 Aug - 6 Aug
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Spacious and luxurious 3-bedroom home w/jetted bathtub

9.2 out of 10, Wonderful, (5)
"Only caveats are the air conditioning is primitive"
Spacious and luxurious 3-bedroom home w/jetted bathtub

Brimfield Waterfront cottage

10.0 out of 10, Exceptional, (4)
"Property is in excellent condition, just the right amount of space for us. "
Brimfield Waterfront cottage
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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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 Retreat!: This highly rated holiday home rental in Woodstock is located on a lake, and has a patio, a garden 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 and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Woodstock?

Expedia has 7 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 Roseland Cottage and Roseland Park Golf Course.

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.