Apartment vacation rentals in Windsor County

Find and book unique apartments on Airbnb

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Popular amenities for Windsor County apartment rentals

Weekly apartment rentals

Superhost
Apartment in Ludlow
4.94 out of 5 average rating, 16 reviews

Dog friendly Okemo village home

MichaelRating, 5 stars2 months ago
Wonderful stay! Everything about our trip was great - responsive host, accommodations as described, walkable to downtown. Donna was extremely responsive and flexible. The house was definitely bigger than the pictures showed, and we had plenty of room for our family of 4. On our next trip to Okemo, I hope Donna's place is available!
Superhost
Apartment in Killington
4.86 out of 5 average rating, 7 reviews

1 bed suite on 2nd floor outdoor heated pool 21921

AdityaRating, 5 stars6 months ago
The location was awesome with best view of fall colors just in the backyard. The check in was smooth. The place was clean with good amenities. I think we have found the right location to plan our yearly fall color trips. Highly recommended!
Guest favorite
Apartment in Lebanon
5 out of 5 average rating, 5 reviews

Downtown charming large house

PatrickRating, 5 stars6 months ago
Great place yo stay, clean and plenty of room. I would stay here again if i was in town.
Top guest favorite
Apartment in Rutland
4.95 out of 5 average rating, 76 reviews

Nice, Large Modern Apartment

Sei-WeiRating, 5 stars1 month ago
Wonderful stay at Darcie's House! Beautiful place with great beds, appliances and toiletries. The House had everything that we needed, and was nice and warm after a long day of skiing at Killington. Only 20min drive to the ski lifts! Darcie was very responsive on all our questions, and was very helpful in our first stay here. Will definitely return!
Superhost
Apartment in Woodstock
5 out of 5 average rating, 4 reviews

Views! Sauna Historic | Woodstock Riverside Escape

CatherineRating, 5 stars6 months ago
The location is terrific--overlooking the river and bridge but just a couple blocks to the main street. We were there during fall foliage season, and we were so glad to be able to leave our car and walk everywhere. The house itself looks just like the photos. We didn't use the kitchen or sauna, so no comments on that, but the bedrooms were nice and the beds, pillows, linens, and temperature were PERFECT for a great night's sleep!
Guest favorite
Apartment in Lebanon
4.83 out of 5 average rating, 394 reviews

The Old Farmhouse

LucyRating, 5 stars4 days ago
David’s place was very clean and comfortable. The location was conveniently down the road from Dartmouth, the reason for our trip. The thoughtful touches such as chocolates and well-stocked bathroom and kitchen were very appreciated. The nicest was not having any checkout tasks :)
Guest favorite
Apartment in Rutland
5 out of 5 average rating, 9 reviews

Modern camp-style apartment - self checkin

JustinRating, 5 stars1 month ago
Great place to stay near Killington. The space in the kitchen/dining area was a little bit tight, 6 people can't eat at the same time. The beds and room were ample in space. The host was very responsive and communicated very well. Will come back if available next time.
Guest favorite
Apartment in Lebanon
4.89 out of 5 average rating, 44 reviews

Light filled Lebanon Loft

JoyceRating, 5 stars2 weeks ago
This is my second time staying at this place and this will always be my first choice whenever visiting Lebanon, NH

Private apartment rentals

Superhost
Apartment in Hartland
4.84 out of 5 average rating, 81 reviews

Private Riverside Studio* Upper Valley*Vermont

GregRating, 5 stars1 month ago
Nice place, small and quaint. I don’t think it’s suitable for a long term stay, but good for a quick weekend and has the necessities needed for a short stay.
Superhost
Apartment in Randolph
4.78 out of 5 average rating, 50 reviews

Cozy VT 1st floor apartment

JocelynRating, 5 stars1 month ago
This was our 2nd time staying here and it was perfect! Perfectly located for a ski weekend with plenty of space to spread out and relax afterwards.
Top guest favorite
Apartment in Shrewsbury
5 out of 5 average rating, 14 reviews

Welcome to Ava's Place!

QingyaoRating, 5 stars1 month 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.
Apartment in Stockbridge
4.87 out of 5 average rating, 181 reviews

Rustic 64 Acre Woodland Haven on a Beautiful River

AsaRating, 5 stars2 months ago
We really enjoyed our time at Kevin’s place. The listing was as described and Kevin was really proactive and helpful when we had questions. There was going to be a big storm that would have snowed us in the day we were supposed to check out so we decided to leave a day early. Kevin offered to refund our final day which we really appreciated
Top guest favorite
Apartment in Weston
5 out of 5 average rating, 38 reviews

Peaceful Woods- Suite with Private Entrance

CateRating, 5 stars2 months ago
This is a wonderful place in a spectacular location. Carol is a stellar host and lovely person in all ways. Thank you for a 5-star stay!
Superhost
Apartment in Woodstock
4.58 out of 5 average rating, 12 reviews

Two bedroom private suite- Woodstock/Barnard, VT

AshleyRating, 5 stars2 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!!
Top guest favorite
Apartment in Ludlow
4.98 out of 5 average rating, 100 reviews

Law Office Apartment

LiliRating, 5 stars6 months ago
Alice’s place is as lovely as she is. She’s a great host! The apartment was everything I needed as a homebase whilst I was looking for property in the area. The kitchen is perfect, even for a professional chef! I was even able to have, a friend from Rutland over for dinner and cooked full fledged meal. Bed and linens were extremely clean and comfortable. Has all the New England charm you could ask for. Neighborhood is very cute. (if you are sensitive to noise, remember that it is an in town property and you will hear some truck traffic in the early morning. I always travel with earplugs, so not really an issue for me.) It’s next to the library and across from the green. There’s a great Shaws supermarket just two minutes drive from the apartment. The house itself is peaceful and full of natural light. The kitchen island with barstools made an ideal workspace for me. No issues with the Wi-Fi. Loved it. I would return. I recommend booking Alice’s place!
Guest favorite
Apartment in Rutland
4.88 out of 5 average rating, 117 reviews

Charlie's Place

AlbertoRating, 5 stars1 month ago
The space was beautifully and cozy. The bed was so comfortable and the living area was perfect for relaxing. The outdoor patio was a dream - Highly recommend this Airbnb if you're looking for a cozy and stylish getaway. It's just 10mins away from Killington! Love it!

Apartment rentals with a hot tub

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

Cozy Quarters

LaurenRating, 5 stars2 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 stars1 month 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, 307 reviews

Dog heavenly! Private, beautiful and relaxing.

HildaRating, 5 stars1 week ago
The place had everything I was looking for. Very peaceful, private and safe 👌🏽 Loved de sound of the river in the backyard and to be able to sit by it and enjoy the sense of peace that it gives. Surrounded by nature, the place is just perfect for that well-needed getaway to unwind and relax 👌🏽 That Superhost title is well-earned! Liz is such a wonderful host 👏🏽 She is super responsive, very attentive, wonderfully helpful and kind 🧡 She helped me make the most of my stay 🧡 Poop Stick is such a lovely dog 🥰 I will definitely be staying again in the future. Highly recommended place ⭐️⭐️⭐️⭐️⭐️
Superhost
Apartment in Killington
4.67 out of 5 average rating, 3 reviews

One Bedroom to Ski Them All at MG: 1BR/1BA

YelenaRating, 5 stars2 months ago
Appartment is just renovated, combining modern amenities with comfortable touches. The location is fantastic, just a stone’s away from ski base. After skiing it was nice to have access to pool and sauna to relax and unwind.
Guest favorite
Apartment in Ludlow
5 out of 5 average rating, 5 reviews

Cozy 2-BR Winterplace Condo Steps from Okemo Mtn.

PatrickRating, 5 stars1 month 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 stars1 month 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 Plymouth
4.91 out of 5 average rating, 166 reviews

Canyons Unit: 1 mile to F&W Summer Camp w/ HOT TUB

DarienneRating, 5 stars2 weeks ago
Amazing location! Sabrina’s place was super cozy and very clean! We would definitely stay again.
Guest favorite
Apartment in Killington
5 out of 5 average rating, 12 reviews

New Resort Condo Close to Lifts

JustineRating, 5 stars1 week ago
I love Ryan's space. It was perfect & cozy place right near Killington resort. I would recommend booking here. Ryan was also very quick with his responses when I had any questions.

Destinations to explore