Apartment vacation rentals in Windsor County

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Popular amenities for Windsor County apartment rentals

Weekly apartment rentals

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

Cozy Green Mountain Village Apt

RyanRating, 5 stars1 week 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 favorite
Apartment in Rutland
4.95 out of 5 average rating, 79 reviews

Nice, Large Modern Apartment

ElaineRating, 5 stars2 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.
Top guest favorite
Apartment in Wallingford
5 out of 5 average rating, 66 reviews

49 River Street

RaquelRating, 5 stars1 week 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 favorite
Apartment in Randolph Center
4.88 out of 5 average rating, 84 reviews

Sunny Converted 2nd Floor Barn in the East Valley

MeganRating, 5 stars3 weeks 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.
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!
Guest favorite
Apartment in Clarendon
5 out of 5 average rating, 21 reviews

Cozy One-Bedroom Retreat with Mountain Views

ShannaRating, 5 stars3 weeks ago
This was a wonderful spot for myself this past weekend! And had I been joined by my friend and Doggo as initially planned, it would have very comfortably accommodated the three of us. Casey was very prompt in responding to my inquiries before and during my stay. I will definitely reach out for availability the next time I visit the area…

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!
Guest favorite
Apartment in Mendon
5 out of 5 average rating, 9 reviews

Sweet Retreat

MichaelRating, 5 stars2 months ago
Amanda’s place was great. It was nicely updated unlike most others. Everything was neat and clean. Great host. Highly recommend !!
Top guest favorite
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!
Superhost
Apartment 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.
Guest favorite
Apartment in Killington
4.9 out of 5 average rating, 78 reviews

Best Location in Downtown Killington

ValkyrieRating, 5 stars3 weeks 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.
Top guest favorite
Apartment in Weston
5 out of 5 average rating, 40 reviews

Peaceful Woods- Suite with Private Entrance

FrankieRating, 5 stars5 days 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!
Guest favorite
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.
Superhost
Apartment in Ludlow
4.97 out of 5 average rating, 32 reviews

Okemo Ski in/out Ground level 1 BR, 1 BA 3beds

DaraRating, 5 stars2 months ago
Gabriella is a very responsive host. I appreciated her attention when we had questions or feedback. You cannot beat this place if you are a skier and the proximity of the location to the ski base and lodge! We immensely enjoyed our stay here even as novice skiers!

Apartment rentals with a hot tub

Guest favorite
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 favorite
Apartment in Killington
4.91 out of 5 average rating, 33 reviews

Cozy Studio/Onsite Spa w/Pool,Hot tub

BriRating, 5 stars2 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 favorite
Apartment in Clarendon
4.95 out of 5 average rating, 309 reviews

Dog heavenly! Private, beautiful and relaxing.

MarindaRating, 5 stars2 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 favorite
Apartment in Killington
5 out of 5 average rating, 13 reviews

Mojo Dojo Winter Casa Condo at Mountain Green

CaityRating, 5 stars2 months ago
What a perfect Killington rental! This unit has been wonderfully renovated to feel so cozy and aesthetically pleasing. The beds were super comfortable and the kitchen had everything we needed to cook a lovely dinner. The amenities at the club are also great with a newly renovated pool, steam room, hot tub, and saunas. A perfect weekend getaway and late season ski trip for our family. We can’t recommend this location enough!
Top guest favorite
Apartment in Killington
4.95 out of 5 average rating, 22 reviews

Cozy Killington Condo

LynetteRating, 5 stars3 weeks ago
We loved how close the hot tub and pool were to the condo.
Guest favorite
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 stars2 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 favorite
Apartment in Killington
5 out of 5 average rating, 13 reviews

New Resort Condo Close to Lifts

DevinRating, 5 stars1 month ago
We had a great stay here. It has everything you need in a decent sized charming space. Would highly recommend.

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