Apartment holiday rentals in Windsor County

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Popular amenities for Windsor County apartment rentals

Weekly apartment rentals

Guest favourite
Flat in Ludlow
4.93 out of 5 average rating, 30 reviews

Steps away from lift- Okemo 1B

GrigoryRating, 5 stars2 months ago
Excellent location for skiing. I do not think I have ever stayed this close to the lift. Being able to stop by the apartment for lunch, or simply to warm up is a huge perk. It can be a bit loud from the lift and the groomers but it wasn’t an issue for us. The apartment is very comfortable for 2 adults and 2 kids.
Top guest favourite
Flat in Shrewsbury
5 out of 5 average rating, 14 reviews

Welcome to Ava's Place!

QingyaoRating, 5 stars3 months ago
We had a very nice stay at Ava’s place. The place is very clean and cozy. It is also more spacious than we thought. Diane and Ava were very nice and left us with welcome gifts which we really enjoyed. The room had everything we need from coffee, tea, to fabric softer. The location is also convenient. It is about a 15 min drive to Okemo mountain resort and 18 min to Rutland with some dining options.
Top guest favourite
Flat in Rochester
4.94 out of 5 average rating, 48 reviews

Cozy Green Mountain Village Apt

RyanRating, 5 stars3 weeks ago
Was in need of a place to stay in Rochester for a wedding down the road from the main part of town and I couldn't have picked a better spot for the weekend. It's a cozy little apartment that has all the simple things you need and it's walking distance to some small town jems to shop and eat at. If I ever want to come back to VT from Boston for the fall, or to escape the city life, I know what would be my first pick would be. :)
Top guest favourite
Flat in Ludlow
4.95 out of 5 average rating, 94 reviews

Peaceful Ludlow Base for Exploring Okemo Valley

MichelleRating, 5 stars1 week ago
Very nice place to have as home base for ventures in and around the area. Very clean and comfortable!!
Top guest favourite
Flat in Weston
5 out of 5 average rating, 40 reviews

Peaceful Woods- Suite with Private Entrance

FrankieRating, 5 stars2 weeks ago
This was a wonderfully peaceful place to stay for a girls weekend! Carol and Steve’s garden is absolutely stunning. The homemade blueberry banana bread was such a delicious and welcoming treat. Would stay here again in a heartbeat!
Superhost
Flat in Woodstock
4.58 out of 5 average rating, 12 reviews

Two bedroom private suite- Woodstock/Barnard, VT

AshleyRating, 5 stars4 months ago
We would highly recommend Corinna’s place to anyone. Our friends and I felt right at home and had a lot of room to move throughout the property. The location is above a Tavern with amazing food. The property itself is spacious, clean, and full of amenities. We ended up getting snowed in for a full day and were able to enjoy the property and turn it into a game day. Loved the place and enjoyed our stay!!
Superhost
Flat in Rutland
4.73 out of 5 average rating, 26 reviews

A Hikers Retreat

KylaRating, 5 stars3 months ago
Bernie’s place was perfect for our stay! We booked it for a last minute ski trip to Killington and the location was great. Although we didn’t dine out at all, the place was very close to town with restaurants and shops. It was just two of us so the space was great! Everything was very clean and well stocked. Would definitely stay here again!
Superhost
Flat in Mendon
4.92 out of 5 average rating, 59 reviews

Charming Killington get away with pool, sleeps 4

DavidRating, 5 stars3 days ago
Great spot - recommend visiting killington in the offseason and stopping by queche and Woodstock

Private apartment rentals

Superhost
Flat in Tunbridge
4.94 out of 5 average rating, 93 reviews

Tunbridge Home with a View

AndreaRating, 5 stars3 days ago
David and Beth were very welcoming. The house was really cute, clean, and comfortable. The view and property were beautiful. You can certainly tell they put their heart into maintaining their gardens. I would not hesitate recommending. We will be back. Andrea
Superhost
Flat in Killington
4.86 out of 5 average rating, 37 reviews

201 Two Queen bed Standard Hotel room

JeffRating, 5 stars3 days ago
Perfect location in between Woodstock and Killington. Quiet and peaceful
Top guest favourite
Flat in Ludlow
4.98 out of 5 average rating, 54 reviews

Okemo Mountain Retreat

AmyRating, 5 stars2 months ago
Perfect location for Okemo - true ski-in ski-out - literally steps away from the Clocktower base lodge and Lift B. Amazing to be able to take lunch break back at in the condo. The unit was clean, roomy, well-furnished - pictures are accurate. Beds (Qn and bunk) are located in the same room but felt like it could work easily for close family/friends. Lucky to find the place for a late season trip up from NYC. Thanks for a wonderful stay and I look forward to future stays!
Top guest favourite
Flat in Rutland
4.95 out of 5 average rating, 80 reviews

Nice, Large Modern Apartment

DeniseRating, 5 stars1 week ago
Darcies place was lovely. beautifully decorated with attention to detail. she provides everything you need with some really nice touches. loved the back garden. There is an upstairs neighbor that was very quiet. Thanks Darcie😊
Superhost
Flat in Rutland
4.76 out of 5 average rating, 63 reviews

Comfortable In Town Apartment

HannahRating, 5 stars1 month ago
Great location in a quiet neighborhood outside of the center of Rutland. Close to Pine Hill Park for some good walking and easy access to all the amenities you'd want in a town. Apartment was clean and cozy. Kitchen was well stocked with supplies and overall the apartment felt very homey. A few confusingly placed light switches and design details but overall quite nice and would return.
Top guest favourite
Flat in Wallingford
5 out of 5 average rating, 66 reviews

49 River Street

RaquelRating, 5 stars3 weeks ago
Immaculate place. Everything you might need! Very charming town. Close to Green Mountain and Appalachian trail hiking. This was our second stay here and we love it. Also, definitely go to Sweet Birch coffee shop while in town. :)
Guest favourite
Flat in Rutland
4.86 out of 5 average rating, 96 reviews

Cozy Corner Nook

LaurieRating, 5 stars3 days ago
We were lucky to find Bree's place available for the 1 night we were staying in Rutland. It was such a great location; simple walk to the main part of the town. Comfortable bed; super, super clean. Cozy space for 2. Easy peasy check in. Great amenities. Really a perfect place for us for the night.
Guest favourite
Flat in Randolph Center
4.88 out of 5 average rating, 84 reviews

Sunny Converted 2nd Floor Barn in the East Valley

MeganRating, 5 stars1 month ago
Super clean, lovely views, Christine communicated well and we were very comfortable. I was traveling with my daughter, it was just the two of us and we felt safe and secure I'd definitely book again for another stay.

Apartment rentals with a hot tub

Guest favourite
Flat in Killington
4.8 out of 5 average rating, 5 reviews

Cozy Quarters

LaurenRating, 5 stars4 months ago
We had the best time staying here for a ski weekend! Super convenient location. Clean and comfortable condo. Can’t go wrong! Heather is responsive and friendly.
Guest favourite
Flat in Killington
4.91 out of 5 average rating, 33 reviews

Cozy Studio/Onsite Spa w/Pool,Hot tub

BriRating, 5 stars3 months ago
We loved staying in this cozy little room for the weekend. The spa was such a nice addition we went every day!
Top guest favourite
Flat in Clarendon
4.95 out of 5 average rating, 310 reviews

Dog heavenly! Private, beautiful and relaxing.

MarindaRating, 5 stars4 weeks ago
Our second stay here was great, river was a little higher but we wanted a peaceful weekend with friends and dogs. Apartment was warm given the unseasonable cold weather and we had all the amenities we needed even dog towels for wet pups. Did not see the host during our stay but she was in contact as needed.
Guest favourite
Flat in Killington
5 out of 5 average rating, 14 reviews

Mojo Dojo Winter Casa Condo at Mountain Green

BettyRating, 5 stars3 weeks ago
An absolutely lovely stay at this property. Extremely scenic, peaceful and green. There is much thought put into the decor of the property. It’s well furnished and decorated with excellent kitchen and bathroom facilities. Ample space and comfortable bedding. Terrific location. This is my third time at Killington from Australia and this has been the best property I have stayed at in Killington. Thank you.
Top guest favourite
Flat in Killington
4.95 out of 5 average rating, 22 reviews

Cozy Killington Condo

LynetteRating, 5 stars1 month ago
We loved how close the hot tub and pool were to the condo.
Guest favourite
Flat in Ludlow
5 out of 5 average rating, 5 reviews

Cozy 2-BR Winterplace Condo Steps from Okemo Mtn.

PatrickRating, 5 stars2 months ago
Location was perfect for my 2 boys and myself. Pool and hot tub was right across the street. On the opposite side of parking lock was access to lift. Perfect location for what I needed. Noah left plenty of recommendations for local spots to check out. Highly recommend!
Superhost
Flat in Killington
4.85 out of 5 average rating, 27 reviews

Condo at Mountain Green

AnthonyRating, 5 stars3 months ago
Simple and basic perfect for a ski weekend at the mountain especially since pet friendly. Kristin was very responsive and helpful throughout the weekend whenever we needed anything. Would highly recommend this stay.
Guest favourite
Flat in Killington
5 out of 5 average rating, 15 reviews

New Resort Condo Close to Lifts

TarekRating, 5 stars1 day ago
The place was as described and Ryan was super responsive and very friendly. We enjoyed our stay

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