Apartment holiday rentals in Windsor County

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Popular amenities for Windsor County apartment rentals

Weekly apartment rentals

Guest favourite
Apartment 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
Apartment 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
Apartment in Rochester
4.94 out of 5 average rating, 48 reviews

Cozy Green Mountain Village Apt

RyanRating, 5 stars2 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
Apartment in Wallingford
5 out of 5 average rating, 66 reviews

49 River Street

RaquelRating, 5 stars2 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. :)
Top Guest favourite
Apartment in Weston
5 out of 5 average rating, 40 reviews

Peaceful Woods- Suite with Private Entrance

FrankieRating, 5 stars1 week 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
Apartment 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
Apartment in Mendon
4.91 out of 5 average rating, 58 reviews

Charming Killington get away with pool, sleeps 4

JackRating, 5 stars2 months ago
Great place to stay for the weekend! Super close to Pico and Kilington mountains. Would highly recommend!
Superhost
Apartment 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!

Private apartment rentals

Superhost
Apartment in Tunbridge
4.93 out of 5 average rating, 92 reviews

Tunbridge Home with a View

TrishRating, 5 stars3 months ago
We had a wonderful weekend stay at David and Beth's home. We had a friendly greeting upon arrival (as well as delicious homemade cookies and maple candies!) David and Beth's home is attached to the apartment but it was quiet and they were unobtrusive. The Tunbridge area is beautiful - quintessential VT! The property is tucked away a bit (SO Vermont!) but our all wheel drive car handled a little bit of late February mud and rolling hills without a problem. We prefer to eat in and brought some food to prepare in the well-equipped kitchen (however we did go to a great burger bar for lunch in Royalton about 20 mins away). The apartment was warm, cozy and comfortable - a perfect meeting place for us and our two adult children - just what we were looking for! Thank you David and Beth - we may see you again next year!
Superhost
Apartment in Randolph
4.78 out of 5 average rating, 54 reviews

Cozy VT 1st floor apartment

ClarissaRating, 5 stars1 month ago
We have stayed here before. The apartment was comfortable, very clean, quiet and has everything you need. We would definitely recommend !
Top Guest favourite
Apartment 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
Apartment in Rutland
4.95 out of 5 average rating, 79 reviews

Nice, Large Modern Apartment

ElaineRating, 5 stars3 weeks ago
Darcie’s house is a great place to stay in Rutland! It is clean and comfortable, furnished to a high standard. The location is excellent – handy to everything in downtown Rutland. The street is quiet. Best of all, Darcie is very responsive, answering quickly, and gracious to travelers with last minute requests. Highly recommended.
Guest favourite
Apartment in Rutland
4.86 out of 5 average rating, 95 reviews

Cozy Corner Nook

JoshRating, 5 stars3 months ago
Stayed for a snowboarding trip at Killington and a day at Sugarbush. 20 mins from Killington in the center of town below. 1 hour from Sugarbush. Great stay
Guest favourite
Apartment in Killington
4.9 out of 5 average rating, 78 reviews

Best Location in Downtown Killington

ValkyrieRating, 5 stars1 month ago
Extremely quick to respond . Just wanted to let them know of a few housekeeping issues, not expecting anything to be done, but property management was immediately called and they sent someone over to remedy what they could. Very quiet and got to see a bear. It apparently was off season and most places were closed. If you use washrags, bring your own as property management does not supply them. The beds and furniture were very comfy.
Guest favourite
Apartment in Hanover
4.94 out of 5 average rating, 31 reviews

2 BR Condo, 5 minute walk from Dartmouth campus

AlisonRating, 5 stars1 month ago
My friend and I stayed in this lovely home when visiting Hanover for a business school reunion. We are both moms and it was the perfect place for a peaceful escape from our busy lives! It was a quick, easy walk into town and the right balance of convenience and quiet. Also extremely well stocked! Would definitely recommend and stay here again.
Apartment in Woodstock
4.8 out of 5 average rating, 131 reviews

Sweet apartment near downtown Woodstock

SandraRating, 5 stars4 days ago
I had a great time staying at Sharon’s. You have a private entrance and a place to park. The kitchen is equipped with everything you will need to make a meal. A full size fridge, stove and a dishwasher. Plenty of room for you and a few friends. The bedroom and bath come with all the things you’ll need including hair care products, plenty of large fluffy towels, a hair dryer and an iron to name a few. Sharon has also provided Netflix in the apartment, but I don’t think you will spend too much time watching tv. You are only a few minutes from downtown Woodstock where you will have plenty to do either shopping, walking or dining in an amazing restaurant. I definitely will be back.

Apartment rentals with a hot tub

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

Cozy Quarters

LaurenRating, 5 stars3 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
Apartment 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
Apartment in Clarendon
4.95 out of 5 average rating, 310 reviews

Dog heavenly! Private, beautiful and relaxing.

MarindaRating, 5 stars3 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
Apartment in Killington
5 out of 5 average rating, 14 reviews

Mojo Dojo Winter Casa Condo at Mountain Green

BettyRating, 5 stars2 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
Apartment in Killington
4.95 out of 5 average rating, 22 reviews

Cozy Killington Condo

LynetteRating, 5 stars4 weeks ago
We loved how close the hot tub and pool were to the condo.
Guest favourite
Apartment 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
Apartment 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
Apartment in Killington
5 out of 5 average rating, 14 reviews

New Resort Condo Close to Lifts

AlayjahRating, 5 stars4 days ago
perfect host! communicates well & perfect area!

Destinations to explore