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House vacation rentals in Wardsboro

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Popular amenities for Wardsboro house rentals

House rentals with a pool

Top guest favourite
Home in Cambridge
4.97 out of 5 average rating, 39 reviews

Country hideaway

GwenRating, 5 stars6 months ago
Second visit and it was just as nice as the first. We like this house inside and out. The pool and walking trail through the woods are great, and the living room is super comfy for family hanging out at night or on a rainy morning. Highly recommend!
Guest favourite
Home in Salem
4.98 out of 5 average rating, 190 reviews

Magical Farm Getaway - a must visit!

StephanieRating, 5 stars2 weeks ago
A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!
Guest favourite
Home in Colrain
4.9 out of 5 average rating, 126 reviews

The 1770 House

BrianRating, 5 stars1 month ago
Another great weekend at Ed’s! It was our group’s second time staying here, and we loved it just as much as the first, which is to say—a lot! Ed is very considerate and responsive, and there’s plenty to do for everyone. We are already looking forward to next year!
Superhost
Home in Ludlow
4.94 out of 5 average rating, 33 reviews

Hilltop 9-BR Mountain Retreat 5-min to Okemo

NicoleRating, 5 stars4 weeks ago
Great communication, even with two days of snow excellent clearance. Definitely recommend 4WD as noted in the listing. Otherwise great place/location for large family gathering! GO BIRDS!
Superhost
Home in Wilmington
4.87 out of 5 average rating, 171 reviews

Adams Farm-"The Little Farmhouse"

Catherine (Lou)Rating, 5 stars1 month ago
We had an amazing stay! The house is lovely and very comfortable, perfect for going skiing at mount snow and cross country skiing and prospect mountain. We were really glad to have picked it. The house is spacious, we all had a lot of room to ourselves, and the kitchen had everything we needed. The farm is gorgeous. Great grocery stores nearby. Sharon was amazing - so helpful when a winter storm threatened to make it hard for us to drive home. She offered us extra time or even another night discounted, which was really generous. She also communicated with friends to help us determine if the road back to NYC had been cleared. We are so grateful for her help! We hope to return in warmer weather to enjoy the farm even more.
Guest favourite
Home in Newfane
4.92 out of 5 average rating, 49 reviews

6 BR Perfect Private Retreat in Vermont!

AlexRating, 5 stars7 months ago
Large house in a very remote area. Approximately 70 acres. It was very relaxing and was nice to enjoy the pool which was professionally cleaned before arrival. The master bath has an incredible view of the mountains and an enormous shower. Pool table was fun and well taken care of. We stayed on probably one of the hotter weekends and the house cooled down at night pretty well just by opening the windows. Most rooms had ceiling fans if no other fans were provided. I can imagine this house would be amazing in the winter or fall too. With the screened in fireplace room and additional fire place inside the main house. You’re also close to 2 ski mountains each about 18 miles away. I could see myself renting again in the future. Thanks again
Guest favourite
Home in Keene
4.93 out of 5 average rating, 208 reviews

The Brick House on Washington Street

KennethRating, 5 stars3 weeks ago
We had a great stay in Keene. Ruth is a fantastic hostess. Her house is just close enough to Main Street to keep it a walkable distance to multiple restaurants and shopping. The house is a nice cozy spot that was big to accommodate my whole family meeting up for a fun winter weekend in Keene. I would stay there again without hesitation
Guest favourite
Home in Plainfield
4.89 out of 5 average rating, 139 reviews

Historic Home on 17 acres of land. Go escape!

BrandieRating, 5 stars1 week ago
Staying here is always a joy for the entire family! It has become an annual tradition that we all look forward to in winter. Thank you for being so accommodating with our schedule and a special thanks to Mitchell for going the extra mile to snow blow a waking path for me and the dogs to keep our daily routine of visiting the horses, after the last storm brought over 13” of snow. P.S. the new stove/oven is amazing!! 🤩

Weekly house rentals

Top guest favourite
Home in Sunapee
4.97 out of 5 average rating, 111 reviews

Sunapee Four Season Getaway with a Mountain View

Kar MunRating, 5 stars2 weeks ago
Thank you so much Josh and Margarita for being proactive in recommendations, check in, and checkout instructions! It was a wonderful stay :)
Guest favourite
Home in Mt Tabor
4.92 out of 5 average rating, 183 reviews

Excellent Ski location So Vt

JustinRating, 5 stars1 month ago
Great place. Was a bit further from Stratton but close to Manchester and Rutland for food options. It is check in with the hosts - clearly in the instructions - which I overlooked upon booking. The place was just as described and the event brought over blueberry muffins which was a nice touch.
Superhost
Home in North Adams
5 out of 5 average rating, 3 reviews

Charming 6 BR home 8 min walk to MassMoca

StaceyRating, 5 stars5 months ago
Nancy was a great host. She was responsive and proactive providing us instructions for accessing the property. The house had lots of space for our group of 9 and it was nice to have a full kitchen to cook in while we stayed. The walk to MOCA was around 15 minutes with our group, which included five kids. It was nice being so close to town. We hope to be back again!
Superhost
Home in Cavendish
4.83 out of 5 average rating, 70 reviews

OKEMO MT HOUSE - OKEMO-LUDLOW-JACKSON GORE

RobertRating, 5 stars4 weeks ago
House fit our need was a good location for skiing at Okemo
Top guest favourite
Home in Keene
5 out of 5 average rating, 137 reviews

Downtown Hot Tub Escape

TavenRating, 5 stars2 days ago
I had an amazing experience at this Airbnb! The place was exactly as described, if not better. The space was clean, stylish, and incredibly comfortable. The host was very communicative and thoughtful, providing us with everything we needed for a hassle-free stay. The location was also perfect—close to all the main attractions but tucked away enough to enjoy peace and quiet. I highly recommend this spot to anyone looking for a cozy, convenient, and welcoming place to stay.
Guest favourite
Home in Wilmington
4.9 out of 5 average rating, 216 reviews

Wilmington A-Frame- Cozy and Convenient

DanielleRating, 5 stars2 weeks ago
This A frame was a perfect home base for a brief Mount Snow getaway. It’s a cozy and efficient space that worked perfect for our family of 4. Very close to a bunch of great restaurants and breweries. There is a bus stop in the driveway, which is convenient if you choose to use and also something to be aware of if you see folks standing in the driveway that is why. :) The host’s communications were super clear and friendly. Really glad we chose to stay here.
Superhost
Home in Fitzwilliam
5 out of 5 average rating, 7 reviews

Large summer home on Laurel Lake NH

BetsyRating, 5 stars67 months ago
This is a place that gives families the time, simplicity, and space to relax together and reconnect. All of the happiness and love of many generations fills the air. This is a wonderful setting for extended families and friends to gather. There is a lot for everyone to do at the house, the lake, and in the Monadnock region. This is a one of a kind property that is very special today more than ever.
Superhost
Home in Williamstown
4.67 out of 5 average rating, 3 reviews

Historic Duplex Walkable to Williams & Spring St.

ElizabethRating, 5 stars55 months ago
What a find! Jeff's place is sparkling clean, super homey, and located on the edge of a beautiful forest with a swimming hole nearby. Bedrooms were great (they set up two extra for us because we were four individuals) although the set up would work well for couples. Kitchen has basically everything you'd need. The living room is great for watching movies. The bathroom upstairs also has a tub with a great view - overall, we loved the place and location!

Private house rentals

Superhost
Home in Manchester
4.87 out of 5 average rating, 23 reviews

Charming Vacation Home in Manchester Center

JakeRating, 5 stars12 months ago
Steal of a deal for this place. Perfect for any couple or family looking to do a vermont ski vacation. Has all the amenities you need, it’s super spacious, it’s right by town, and it’s a short drive to stratton or bromley. Easy 5 stars.
Guest favourite
Home in Keene
4.91 out of 5 average rating, 47 reviews

Little House with Lots to Offer

CindyRating, 5 stars2 weeks ago
Grreat little house for our family of three. Well-insulated and comfortable. Cozy and felt like home. Plenty of amenities to make us feel at home. Situated in the middle of a few different ski places. Neighborhood feels safe. The place was clean and the owner was responsive .
Superhost
Home in Ludlow
5 out of 5 average rating, 17 reviews

2 Units, 1 Home | Perfect for Multiple Families

BridgetRating, 5 stars1 month ago
My group stayed here for a ski weekend at Okemo and had a great time. 5 minute drive from the mountain so very convenient. Brandon was a great host and even set up a telescope for us to use one night.
Guest favourite
Home in Plainfield
4.84 out of 5 average rating, 100 reviews

The Oaks - secluded rural estate w/ amazing views

HeidiRating, 5 stars1 week ago
This place is very comfortable & has character and charm. We enjoyed visiting the friendly goats & chickens and sharing veggies with them. We slept well on comfortable beds, happy to find extra blankets because we were there during a cold snap & didn't want to have the furnace setting too warm.
Top guest favourite
Home in Brattleboro
4.94 out of 5 average rating, 121 reviews

Spacious Brattleboro home on river, walk to town

DeborahRating, 5 stars3 weeks ago
Absolutely incredible place! Tons of room, bathrooms for each bedroom was a big hit. Amazing location. Views were magnificent after 8 inches of snow and some freezing rain. Perfect excuse to not leave the house and enjoy the peaceful serenity over a nice margarita. Fall views must be totally awesome. Don’t need to bring anything except you, your friends and some food. The home has everything you need, all set and ready to go, and I mean everything you’ll need. The house manager Teri was an absolute peach. Her connection to the house and knowledge of the local history was amazing. 5 STARS doesn’t do this place justice. Already planning a return visit.
Top guest favourite
Home in Ludlow
5 out of 5 average rating, 41 reviews

New Home on 23 Acres-Views of Okemo w/ Hot Tub

JenniferRating, 5 stars3 days ago
This home is absolutely beautiful, with stunning views that make for a perfect Vermont getaway. The house is well-equipped with everything you need for a comfortable and relaxing stay. The location is fantastic—close to local attractions yet peaceful and private. Whether you’re looking for a cozy weekend retreat or an adventure in nature, this spot has it all. Highly recommend!
Superhost
Home in Jamaica
4.94 out of 5 average rating, 172 reviews

Cozy Riverfront Home in beautiful Jamaica

AmyRating, 5 stars2 weeks ago
Great place and Jen was easy to communicate with. The place has stunning views and it was close to & easy to get to the main road. Jen’s recommendations were helpful for places to eat/pick up essentials. The house was clean and had everything you could need. We would definitely stay here again.
Guest favourite
Home in Woodford
4.91 out of 5 average rating, 32 reviews

Green Mountains Lake Retreat - Hidden Gem

MarissaRating, 5 stars3 weeks ago
We have stayed in this house in the past and we have always had a great experience! It’s clean, Larissa is very quick to respond, and we love the access to the vast trails. It was an amazing weekend and hope to book again in the future!

Quick stats about house rentals in Wardsboro

  • Total rentals

    50 properties

  • Nightly prices starting at

    $87 CAD before taxes and fees

  • Total number of reviews

    1.4K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windham County
  5. Wardsboro
  6. House rentals