Holiday rentals with a pool in West Windsor

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Top-rated rentals with a pool in West Windsor

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Home in Killington

4.9 out of 5 average rating, 184 reviews

Luxury Condo Tucked in the Heart of Killington

Welcome to our ❄newly renovated❄ Cozy Condo Located right off the "loop" walking trail on river road. Our end unit condo sits just 5 min from the base of Killington with easy access to night life/restaurants and much more. Whether you are skiing, hiking, biking, kayaking or just enjoying the fresh Vermont air, you'll love the comfort of our condo. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in Killington!

Guest favourite

Home in Springfield

4.94 out of 5 average rating, 99 reviews

Ski Mountain View Estate

Have fun in Vermont with the whole family at this peaceful off the grid feeling private home. Come see the amazing, scenic views Vermont has to offer. We are located minutes to some great ski mountains if you are looking to ski or snowboard. Love hiking? Enjoy hiking right out back of our home. Great time for the kids and parents to have a sledding party with a fire and views. Then relax in the new hot tub right off the deck. Always plenty of firewood for the pit! Pool is closed for winter

Guest favourite

Treehouse in Stockbridge

4.94 out of 5 average rating, 107 reviews

Romantic Treehouse- Hot tub, FPLC, 20 Min to KLT

New treehouse was built by me with my own two hands during the pandemic. The architect styled design is one of a kind with huge windows. Radiant Heat, custom bathroom/kitchen. My grandparents once owned and operated a dairy farm in the area and I want to share this treehouse and surrounding area with my guests. Ski or Ride in only 20 min to Killington and resorts. My treehouse is located on the historic ski highway with Killington-20 min, Pico, Okemo, Sugarbush, Saskadena Six, and Stowe.

Guest favourite

Condo in Stratton

4.96 out of 5 average rating, 120 reviews

Premier Stratton Village Location - Pool & Hot Tub

-- Walk across the street to Stratton Ski Lifts -- Conveniently located near the Stratton Village, this condo places you at the center of all the mountain activities - skiing, mountain biking, events, weddings, shopping & dining. This updated studio includes gas fireplace, AC, stainless appliances, and nice décor. Long Trail House condos boasts underground heated parking, year-round outdoor pool with patio and grill, multiple hot tubs, and sauna. Come visit and relax in the Vermont mountains.

Superhost

Condo in Ludlow

4.8 out of 5 average rating, 163 reviews

Winter Paradise —Ski-ON/Ski-OFF Okemo Getaway

Perched on Okemo mountain, step to the trails and start your day with no need to ski to the base. You will be on the best ski/on-ski/off location directly to Sunburst 6 Bubble, Sachem or South Ridge Quads & boarding park lifts; while having everything you might need for a cosy and convenient family stay. That includes a fully-equipped kitchen and a living room with games for your entertainment, a private balcony, laundry facilities and shared resort-style amenities at Winterplace with pool.

Guest favourite

Condo in Killington

4.95 out of 5 average rating, 201 reviews

Walk or Shuttle to Lifts/2BR @ Mt. Green Resort!

Our CLEAN & SPACIOUS 2 Bedroom and 1.5 Bath Condo is a corner unit in the 4 Season Mountain Green Resort which is located directly across the street from the Snowshed Base Lodge at Killington Mountain (just a 10 minute walk or 2 minute shuttle ride to the slopes) and right next door to the Killington Golf Course. With our recently updated kitchen, renovated master bathroom, luxury vinyl flooring and new furniture, you are sure to enjoy our home away from home in the Green Mountains!

Guest favourite

Condo in Killington

4.93 out of 5 average rating, 128 reviews

CozyCub Shuttle on/ski home, Fireplace, Walk out

Delight in this friendly, fully renovated (2022) modern ski condo next to Killington's popular Snowshed base area, learn-to-ski trails, and golf course. Shuttle-On / Ski-Off to the condo during peak season. The location is prime for accessing everything the area has to offer. Relax for some streaming after a day on the mountain on the 65" TV. Enjoy the Whiffletree condo association's outdoor pool and tennis courts in the summer, settle in by the gas fireplace, or head out to explore.

Guest favourite

Condo in Killington

4.94 out of 5 average rating, 233 reviews

Dog-Friendly 2BD/2BA Oasis - Pool, Hot Tub & Spa

Escape to tranquility in this charming 2-bedroom, 2-bathroom home, designed with comfort and relaxation in mind. Nestled in a peaceful neighborhood, it’s the perfect retreat for families, couples, and pet owners who want to enjoy a little extra R&R with their furry friends. The spa area with a pool and hot tub is ideal for unwinding after a long day of exploring or just enjoying the serene environment. Alternatively, you can relax after a long in front of the wood-burning fireplace!

Guest favourite

Cottage in Newfane

4.99 out of 5 average rating, 204 reviews

Cozy Vermont Antique Sugar House with Fireplace

Enjoy a peaceful and unique stay at this beautiful 1796 Sugar House. Luxury bedding, cozy fireplace, soaring timbers to a cathedral ceiling make this a special place. There is a Queen size bed on the main floor and twin beds in the sleeping loft accessible by a ladder. Try some of our wonderful local restaurants and shops. Lots of hiking trails to explore. Winter sports all around, or just enjoy some hot chocolate, a fire, and a good book. You are sure to enjoy the “Sugar House”.

Guest favourite

Condo in Killington

4.91 out of 5 average rating, 155 reviews

Renovated 1BR, Walk to Lifts, Covered parking

Our comfortable 1-bedroom condo in Building 3 of the Mountain Green Resort provides a bright yet cozy home base for your Killington getaway. Our condo features a new kitchen, dedicated Wi-Fi, and smart TVs. Conveniently located within walking distance to Snowshead, it's perfect for all your mountain activities. Please note, construction teams are replacing the roof of each bldg 7am-7pm daily through Thanksgiving. Scaffolding is up around the outside, and the balcony is unavailable.

Superhost

Townhouse in Killington

4.87 out of 5 average rating, 235 reviews

Renovated 2bd/2.5bath/Den + Pool Access (pets ok)

Recently updated ski condo - modern kitchen appliances and new furniture. Minutes away from Killington Ski base. Drive there or use a paid bus service, steps away from the condo. Part of the luxurious Woods Spa Resort and stay includes use of resort amenities including gym, pool, steam/sauna and hot tub. Spa service available but not included in fee (please check for open hours) Warm, cozy and welcoming-custom built for ski lovers to relax after a long day on the mountains.

Guest favourite

Home in Plainfield

4.89 out of 5 average rating, 136 reviews

Historic Home on 17 acres of land. Go escape!

This place is a dream. Please enjoy the outdoors and everything this amazing place has to offer. The pool opens around May 2024! It is a heated pool and salt water. Pool rules: absolutely no diving. No children under the age of 18 should be near or in the pool area without supervision under any circumstances. NO glassware by the pool. If there is an incident with glass near the pool area please tell our property manager immediately. If you need anything just ask