Woodstock Holiday Rentals

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Holiday Rentals in Woodstock

Secluded 2-Acre Lakefront Home! Book Your Getaway!

9.8 out of 10, Exceptional, (73)
"We enjoyed our stay, especially sitting on the deck and listening to the birds. We would definitely love to return again sometime."
The price is NZ$1,014
includes taxes & fees
29 Sept - 30 Sept
Secluded 2-Acre Lakefront Home! Book Your Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!

10.0 out of 10, Exceptional, (18)
"We had a great stay at the lakehouse. Will definitely consider a future stay."
The price is NZ$997
includes taxes & fees
29 Sept - 30 Sept
Stunning Lakefront Escape! Book Your Dream Getaway!

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

9.8 out of 10, Exceptional, (25)
"This prperty was GREAT! Clean, and very accomadating. Had everything you would need staying there. Didn't get to use the lake but sitting on the deck was relaxing. Will book again. 10 Stars!! Thank You!"
The price is NZ$386
includes taxes & fees
29 Sept - 30 Sept
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Dove Cabin up in the Trees

9.8 out of 10, Exceptional, (23)
"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 NZ$446
includes taxes & fees
30 Sept - 1 Oct
Dove Cabin up in the Trees

Amazing lake house with everything you need!

9.8 out of 10, Exceptional, (17)
"Great time, lovely location, easy to access and beautiful lake!"
Amazing lake house with everything you need!

Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!

10.0 out of 10, Exceptional, (134)
"It was our 4 lake vacation there. We absolutely love it and our dog Charlie enjoys the beautiful yard and and a swim in a little bay at this property."
Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!

Brimfield Waterfront cottage

10.0 out of 10, Exceptional, (10)
"The cabin was definitely cozy, the treats were a nice addition, and the kitchen had most of what we needed. Would return next time we plan to be in the area. Gus was great to communicate with! Thank you@"
Brimfield Waterfront cottage

Treehouse - Countryside - Farm Animals - Fire Pit

9.4 out of 10, Exceptional, (27)
"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!"
The price is NZ$514
includes taxes & fees
20 Oct - 21 Oct
Treehouse - Countryside - Farm Animals - Fire Pit

The Tree House at Underhill Hollow

9.4 out of 10, Exceptional, (32)
"My 10 year old loved this stay! Meeting the goats and sheep was fun and it was located in a nice area. Would love to visit again!"
The price is NZ$300
includes taxes & fees
29 Sept - 30 Sept
The Tree House at Underhill Hollow

Wizard's Roost at Underhill Hollow

9.6 out of 10, Exceptional, (18)
"Full of whimsy, loved all of the details of the construction and decor. Great place to stay"
The price is NZ$272
includes taxes & fees
29 Sept - 30 Sept
Wizard's Roost at Underhill Hollow

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

10.0 out of 10, Exceptional, (196)
"Wonderful view of the water. Well cared for and altogether great place to stay. "
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

Spacious 2 Bedroom 1 Bath apt

10.0 out of 10, Exceptional, (1)
"Great host and excellent apartment "
Spacious 2 Bedroom 1 Bath apt

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

9.0 out of 10, Wonderful, (21)
"Hosted a bachelorette trip at this property and it was fantastic. The kayaks and paddle boards provided plenty to do along with a firepit to sit around at night. The house was cozy with plenty of space to sleep 5. Had a great time! "
The price is NZ$483
includes taxes & fees
29 Sept - 30 Sept
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

SteamPunk Bunk House and Intergalactic Way Station

10.0 out of 10, Exceptional, (11)
"This was a charming little apartment with a unique steam punk alien theme. If you have a playful mindset, I highly recommend staying at this location. I couldn’t have been more overjoyed with my stay."
The price is NZ$290
includes taxes & fees
30 Sept - 1 Oct
SteamPunk Bunk House and Intergalactic Way Station

Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!

9.8 out of 10, Exceptional, (114)
"The weather didn’t cooperate enough for us to enjoy the water, but it was lovely to look at"
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!

Lakefront: Fish, Kayak, Canoe, Near Treehouse Brewery, Sturbridge Village!

10.0 out of 10, Exceptional, (3)
"Great little cottage at a lake. Super well appointed with pots, pans, gas grill, etc.... great hosts very attentive! "
Lakefront: Fish, Kayak, Canoe, Near Treehouse Brewery, Sturbridge Village!

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

10.0 out of 10, Exceptional, (4)
"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! "
4-bedroom house in Windham - Pet Friendly - Thread City Family Escape

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

10.0 out of 10, Exceptional, (12)
"The house was beautiful. Very clean, pet friendly, very good communication with owner."
The price is NZ$1,069
includes taxes & fees
20 Oct - 21 Oct
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!

Luxury Home, Pool, fireplace

10.0 out of 10, Exceptional, (29)
"A truly beautiful place with the most gorgeous pool and landscaping. We will be back for sure!"
Luxury Home, Pool, fireplace

Apartment in town center #1

8.6 out of 10, Excellent, (23)
"Nice location, within minutes of town Great accommodations, very clean. Great stay Highly recommend "
The price is NZ$476
includes taxes & fees
29 Sept - 30 Sept
Apartment in town center #1
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

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 favorite 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 depends 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 NZ$272 per night. Entering your travel dates in the search wizard you might find 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.

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 Taylor Brooke Winery and Roseland Cottage.

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.