Woodstock Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Woodstock

Breathtaking Lakefront Property! Cozy house! Special off-season rates!
10.0 out of 10, Exceptional, (9)
"Beautifully appointed home on a beautiful lake in Woodstock, CT. We enjoyed kayaking on the lake, visiting nearby orchards and hiking the many scenic trails nearby. Many great restaurants in the area as well. Although we did not partake, there is a great rail trail nearby for hiking, walking, etc. The home listing is very accurate, the kitchen is well equipped, and the cleanliness of the home is top notch. In addition, the hosts Heather and Dan, were very responsive and were...
The price is AU$839
includes taxes & fees
18 Nov - 19 Nov
Breathtaking Lakefront Property! Cozy house! Special off-season rates!
Secluded 2-acre Lake Front Home! Special off-season rates!
9.8 out of 10, Exceptional, (59)
"The house is in a beautiful location and is setup wonderfully to joyfully cook a big meal with a group of people. The house is comfortable and inviting, if a bit worn down (chipping paint, rust, and some dusty shelves). The beds are comfortable as are the sitting and living rooms. The jetted bathtub in the pictures was out of order and there are instructions not to use the wood stoves. The hosts have very distinct instructions and their personality was clearly showcased. "
The price is AU$846
includes taxes & fees
18 Nov - 19 Nov
Secluded 2-acre Lake Front Home! Special off-season rates!
Wrecked at Ron’s
10.0 out of 10, Exceptional, (6)
"House is spacious and comfortable with a fully equipped kitchen that has everything you need. Beds were comfortable and bathrooms were conveniently located on both floors. Everything was clean and tidy. It's clear Ron is doing continuous updates to the property, but that didn't bother us at all. Location is very peaceful with gorgeous views and spectacular sunrises and sunsets. Ron is right on site and readily available if needed. We'd definitley stay again."
Wrecked at Ron’s
Famous Estate and Mansion with unmatched amenities for our prized guests!
7.2 out of 10, Good, (10)
"Family gathered from several different states for a large wedding event. We all enjoyed being able to be together in one place. The house wasn’t perfectly spotless and stained carpets and too many things on the walls but nothing terrible. It was all easily overlooked because we were all together with lots of room to spread out if needed."
The price is AU$1,449
includes taxes & fees
18 Nov - 19 Nov
Famous Estate and Mansion with unmatched amenities for our prized guests!
Home in the woods
9.2 out of 10, Wonderful, (20)
"Very Large home with well equipped kitchen. Beds were all very comfortable. Host was very attentive to our needs and questions during our stay."
Home in the woods
Beautiful two-story home close to downtown worcester 5beds-4bedroom
8.8 out of 10, Excellent, (3)
"Great place for a short stay to allow us to attend a Bridal shower. Lots of comfortable beds. Thanks."
Beautiful two-story home close to downtown worcester 5beds-4bedroom
Lakefront Cottage w/ Covered Porch & Dock!
3.0 star property
Lakefront Cottage w/ Covered Porch & Dock!
Lake | PetsOK | Wi-Fi | W&D | Fire Pit | Kayaks
9.6 out of 10, Exceptional, (28)
"The property was exactly like stated on VERBO. Cozy with all amenities you could need. "
The price is AU$528
includes taxes & fees
18 Nov - 19 Nov
Lake | PetsOK | Wi-Fi | W&D | Fire Pit | Kayaks
Lake | PetsOK | Wi-Fi | W&D | Fire Pit | Kayaks
9.0 out of 10, Wonderful, (36)
"Wonderful host. Very thoughtful - lots provided in the house that you need to have a great stay. "
The price is AU$515
includes taxes & fees
17 Dec - 18 Dec
Lake | PetsOK | Wi-Fi | W&D | Fire Pit | Kayaks
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
10.0 out of 10, Exceptional, (47)
"What a gem this cute house was on the lake! The owners didn’t skip a beat with the attention to detail. It had everything and was so clean. Communication was spot on. We will definitely book again the next time we come to CT! We already miss waking up with coffee and watching the sun come up over the lake. "
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore
10.0 out of 10, Exceptional, (180)
"Overall a wonderful stay. This is a duplex and the owner lives next door. Nice neighborhood and beautiful view"
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore
Spacious Massachusetts Apartment #2
9.4 out of 10, Exceptional, (15)
"The apartment was clean, stocked with all you need and the location was just off the Main Street so stores and restaurants were walkable. Ample parking behind the unit. Comfortable bedrooms and furniture. "
Spacious Massachusetts Apartment #2
Fall Lake Cottage near Treehouse Brewery & Amazon Warehouse with King Beds
9.0 out of 10, Wonderful, (8)
"We loved this cottage! It's right on Glen Echo Lake in Charlton, perfect for a romantic getaway. The cottage was spacious and the king sized bed was wonderfully comfortable. The bathroom has two sinks and two shower heads. The furniture was all comfortable and clean. There's a smart TV so you can get all your streaming services and YouTube. The living room couch power reclines and is dangerously comfortable. Everything looked new and modern. The kitchen comes with all the essentials: pots and...
Fall Lake Cottage near Treehouse Brewery & Amazon Warehouse with King Beds
Waterfront New England House on Wickaboag Lake!
9.8 out of 10, Exceptional, (76)
"Enjoyed this spacious house that easily accommodated our family for my mother's 80th birthday weekend. We were able to cook for everyone, sleep everyone comfortably, and loved hanging out on the deck. Recommend this to families looking to spend some quality time together. "
Waterfront New England House on Wickaboag Lake!
Quiet and Cozy Campground Cabin near the lake
9.4 out of 10, Exceptional, (3)
"Cute and cozy cabin with friendly staff, close to everything"
Quiet and Cozy Campground Cabin near the lake
Lake House in Sturbridge w/All the Views!
9.8 out of 10, Exceptional, (6)
"We had a great time in Sturbridge. Can't beat the location of this house - it's absolutely beautiful, and very close to Old Sturbridge Village and a cute coffee shop we frequented during the long weekend. Everything was nice and clean, the hot tub was great, and it was easy to check in. The beds are comfortable and it was nice to not have to worry about the linens upon checkout. The host replied super promptly when we had questions about the location of trash/recycling bins, and when there was...
The price is AU$1,456
includes taxes & fees
18 Nov - 19 Nov
Lake House in Sturbridge w/All the Views!
The Lake House
9.8 out of 10, Exceptional, (8)
"Wonderful place to camp for a large family, particularly in summertime. Great view of the lake and the best sunsets. "
The Lake House
Full family home 200 ft from the lake shore. Dog friendly!
10.0 out of 10, Exceptional, (4)
"The house is beautiful, comfortable and spotless. "
The price is AU$914
includes taxes & fees
2 Dec - 3 Dec
Full family home 200 ft from the lake shore. Dog friendly!
Cozy lake cottage. Bring your boat. New dock at cottage.
10.0 out of 10, Exceptional, (7)
"Relaxing, clean and great host communication. Hidden gem on the lake! Thank you! "
Cozy lake cottage. Bring your boat. New dock at cottage.
Spectacular waterfront cottage on the most beautiful lake in CT's 'Quiet Corner'
10.0 out of 10, Exceptional, (42)
"Magical weekend on Lake for Family Wedding….felt Like home but With beautiful deck and use of pontoon boat to explore the best kept secret of a lake in the area…so peaceful and yet so close to rest of family. Perfection!!!"
Spectacular waterfront cottage on the most beautiful lake in CT's 'Quiet Corner'
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.
Don't see what you're looking for?
See all available properties in Woodstock
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Woodstock you may be interested in

Secluded 2-acre Lake Front Home! Special off-season rates!
9.8 out of 10, Exceptional, (59)
"The house is in a beautiful location and is setup wonderfully to joyfully cook a big meal with a group of people. The house is comfortable and inviting, if a bit worn down (chipping paint, rust, and some dusty shelves). The beds are comfortable as are the sitting and living rooms. The jetted bathtub in the pictures was out of order and there are instructions not to use the wood stoves. The hosts have very distinct instructions and their personality was clearly showcased. "
The price is AU$846
includes taxes & fees
18 Nov - 19 Nov
Secluded 2-acre Lake Front Home! Special off-season rates!
Famous Waterfront Inn with Jacuzzis, Stunning amenities and unmatched comforts!!
7.0 out of 10, Good, (18)
"The house was very antiquey unfortunately only one of the 4 bathrooms shower worked I was excited to lay in the jacuzzi tub but it was gross and dirty some of the dishes were also dirty. they are also trying to sell the house so we came home to people looking at it which we weren’t told about and kind of inconvenient when you have 5 tired kids On the plus side it was a quiet neighborhood and it was spacious "
The price is AU$853
includes taxes & fees
28 Nov - 29 Nov
Famous Waterfront Inn with Jacuzzis, Stunning amenities and unmatched comforts!!
Breathtaking Lakefront Property! Cozy house! Special off-season rates!
10.0 out of 10, Exceptional, (9)
"Beautifully appointed home on a beautiful lake in Woodstock, CT. We enjoyed kayaking on the lake, visiting nearby orchards and hiking the many scenic trails nearby. Many great restaurants in the area as well. Although we did not partake, there is a great rail trail nearby for hiking, walking, etc. The home listing is very accurate, the kitchen is well equipped, and the cleanliness of the home is top notch. In addition, the hosts Heather and Dan, were very responsive and were...
The price is AU$839
includes taxes & fees
18 Nov - 19 Nov
Breathtaking Lakefront Property! Cozy house! Special off-season rates!
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.

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 Lake Front Home! Special off-season rates!: 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 5 holiday rentals for your stay in Woodstock.

What can I see and do in Woodstock?

Woodstock Town Beach and Muddy Pond 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.