
Vacation rentals with a pool in Windsor County
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Top-rated rentals with a pool in Windsor County
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Popular amenities for Windsor County rentals with a pool
House rentals with a pool

Luxury Condo Tucked in the Heart of Killington
The place was amazing. Probably one of the best Airbnb’s I’ve rented in terms of value for money. Very responsive host. The location is private, had pretty much all the amenities one needs and everything was well organized. The only downside is the check in is at 3pm but the checkout is at 10am. Which is pretty much unheard of. I’ve asked for one hour extension but was immediately sent a 25$ surcharge request for 1 hour. Apart from that everything was good.

Ranch at Mendon Mt Orchards
Perfect location for skiing, and cosy home that we all enjoyed (including our pup). We appreciated the thoughtful touches provided by the host, and the apple orchard was a beautiful setting. Would definitely stay again!

Pet-Friendly, Mountainside Home | Treetop Lodge
We stayed here while visiting family in Hanover forThanksgiving. A spacious house nestled within an amazing wooded area. We had the pleasure of waking up to all the trees covered in fresh snow. All the more perfect because the house has huge windows lots of natural light. Highly recommend.

Entire Home, Near Slopes, Hot Tub, EV Charger
The stay was excellent. The home was beautifully renovated. The rooms were large and very comfortable. Location was perfect for the 8 of us for a ski weekend at Killington. Hope to be back.

Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths!
Beautiful home and cottage with stunning surrounding scenery. Came here on a getaway from NYC and it was exactly what we needed. The jumbo jet bathtubs and fireplaces give this cozy space a luxurious feel, and the kitchen was downright impressive (brought a chef friend for us who was very impressed). Had to call the host with some questions when I arrived but they were answered immediately. Very clear check in instructions from the host and once we pulled up to the property it was very seamless to get inside and begin unpacking. We had an stress-free stay and checkout thanks to the intention with which these hosts set up their space and rental process. We will be coming back next year!

The Fairway House - Premier Golf Course 3 BR Home
We thoroughly enjoyed our stay with 5 adults and one dog. We walked in and immediately felt at home. This was one of the most well appointed places I have ever rented...it had everything we needed and more . The kitchen and the living space was quite comfortable. The beds were wonderful. There is a trail to the river right across the street which we used several times. I can't think of a negative thing to say.

Bright & Modern Quechee Town House - Self Check-In
We loved it! Great description and photos, really accurate. Michael was so helpful and really friendly and responsive.

Private Farmhouse with in ground pool!
My family and I truly enjoyed our time spent at the farmhouse. Everything was as expected from the listing. The pictures do not do justice for the property. It's beautiful and well maintained. The pool was nice, warm, and clean. There are yard games readily available and a nice fire pit area. Brin and Maria are super responsive and left very detailed instructions on the property for you. Everything you need is there minus food, which is a 12-minute drive towards a few different grocery stores. The hill is so fun to roll down, too! Thank you so much!
Condo rentals with a pool

Northlands at Trail Creek
Super wonderful spot that is walkable to lifts and then able to ski home at the end of the day. There's a great sauna , hot tub and pool right around the corner from the condo. All super convenient. Will be back next year.

Mountain Oasis
Cozy, clean, well appointed condo with great amenities within walking distance of the mountain, wonderful!

2 bed-2 bath (6 max): walk to lifts and lodges
A wonderful home base for a wonderful Winter ski treat! Highly recommended, very comfortable and very well equipped. Super smooth check-in in a wonderful location.

Location + Spa! - Cozy 2BR Condo - Mountain Side
Very clean and great location. It was about an 8 minute walk to the Ramshead lodge and we ate at two restaurants within a 5 minute walk. The shuttle was also easy and ran frequently. Would recommend!

Pico Mountain Ski in and Ski out
“Michele is a wonderful host! The location was perfect—just a short drive to Killington Mountain and the added bonus of being able to walk right onto Pico Mountain made our trip even better. The convenience and ease of access to the slopes made for an amazing stay. Highly recommend!”

Skier's Retreat 2bed/1.5 bath condo w/ Amenities
This condo has a great location, and the unit itself is extremely pleasant. If you're going to Killington I highly recommend it

Ski, Ride, Walk On/Off Condo On Pico at Killington
Great location for pico mountain. The ski on ski off was pretty easy to find and nicely located. The location is slightly less ideal for killington, as you need to take a shuttle that has multiple stops. We also ended up on a bigger bus to take us back from Killington and the drop off was on the main road, which was a bit difficult to walk on in our snow gear. Overall, nice apartment and perfect for my group of friends.

3 Bedroom Castle Town Home
For our family of three this home fit us perfectly. You CAN certainly have more guests but it truly fit our needs. The set up was VERY spacious and cozy at the same time. The women at the desk are so kind and very good at their jobs. Not only did we feel at home when we arrived to our place, meeting them made us feel even more welcome. The castle was exquisite and an amazing experience in itself. The quaint town of Ludlow is a heart beat away with everything you need. All and all we can't say enough about how satisfied we are with Andy's home, the pricing, the staff and location! Our experience was amazing, memorable and we will be returning for sure next year! We are planning to come with our best friends next year & their kids because of your amazing home & our fantastic experience! 😁 Thank you again for opening your home to our family! The Baers
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- Okemo Mountain Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Pats Peak Ski Area
- Ragged Mountain Resort
- Mount Snow Ski Resort
- Tenney Mountain Resort
- Fort Ticonderoga
- Northeast Slopes Ski Tow
- Ekwanok Country Club
- Baker Hill Golf Club
- Veterans Memorial Recreation Area Ski Hill
- Bretwood Golf Course
- Hooper Golf Course
- Dartmouth Skiway
- Dorset Field Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Country Club of New Hampshire
- Santa's Land USA
- Crotched Mountain Ski and Ride
- Brattleboro Ski Hill
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