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Our top choices for Pittsford vacation homes

1. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (18 reviews)
"WE ENJOYED OUR STAY"
United States
Susan E.
The price is AED 323
AED 638 total
includes taxes & fees
16 Nov - 17 Nov
Cozy Rutland Retreat

2. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
10.0 out of 10, Exceptional, (1 review)
"We were very surprised. The accommodation's well worth the amount we paid. I was surprised how from the start to the close of our Anniversary get away It was such an easygoing experience. The host left fresh towels and bedding linens. The host kept in contact the entire way booking this condo. It was roomy nice Quiet!! I loved the privacy yet close to everything Killington has to offer. Our anniversary was special as we went with the host recommendation for a local resturaunt the Garlic. We have...
United States
Melinda D.
The price is AED 291
AED 906 total
includes taxes & fees
23 Nov - 24 Nov
Luxury Condo Tucked in the Heart of Killington

3. large ski ranch hot tub close to killington pets ok

large ski ranch hot tub close to killington pets ok
Mendon
9.2 out of 10, Wonderful, (10 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is AED 526
AED 1,976 total
includes taxes & fees
20 Nov - 21 Nov
large ski ranch hot tub close to killington pets ok

4. new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Mendon
9.4 out of 10, Exceptional, (8 reviews)
"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."
United States
Aurore H.
The price is AED 502
AED 1,024 total
includes taxes & fees
16 Nov - 17 Nov
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

5. Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort

Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort
Chittenden
9.4 out of 10, Exceptional, (6 reviews)
"Loved this stay - the farmhouse is authentic and oozes charm! Everything about this stay was easy - 20min drive to the slopes, 15 min to downtown Rutland, and an extremely well-equipped house to easily accommodate the six of us. Superb communication from the host both prior to and during our stay (promptly answered several questions for us). If you want a vintage farmhouse feel as opposed to a modern condo-style stay, this is the place for you!"
United States
Carl P.
The price is AED 575
AED 2,300 total
includes taxes & fees
16 Nov - 17 Nov
Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort

6. Kingsley Homestead - 2 Bedroom retreat

Kingsley Homestead - 2 Bedroom retreat
Rutland
The price is AED 633
AED 695 total
includes taxes & fees
18 Nov - 19 Nov
Kingsley Homestead - 2 Bedroom retreat

7. Historic Victorian Estate 4 Bed 2 Bath Fast Wifi

Historic Victorian Estate 4 Bed 2 Bath Fast Wifi
Fair Haven
9.2 out of 10, Wonderful, (39 reviews)
"Great quick stay on the way to the Adirondacks"
United States
Natalie B.
The price is AED 496
AED 1,063 total
includes taxes & fees
16 Nov - 17 Nov
Historic Victorian Estate 4 Bed 2 Bath Fast Wifi

8. Ski Home/Arcade Mountain Views Near Killington/Woodstock

Ski Home/Arcade Mountain Views Near Killington/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
United States
Kevin M.
The price is AED 489
AED 2,050 total
includes taxes & fees
17 Nov - 18 Nov
Ski Home/Arcade Mountain Views Near Killington/Woodstock

9. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
The price is AED 489
AED 2,050 total
includes taxes & fees
17 Nov - 18 Nov
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

10. CozyDen- Fireplace, Ski Off/ Shuttle On

CozyDen- Fireplace, Ski Off/ Shuttle On
Killington
9.6 out of 10, Exceptional, (4 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is AED 490
AED 986 total
includes taxes & fees
16 Nov - 17 Nov
CozyDen- Fireplace, Ski Off/ Shuttle On

11. NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
North Sherburne
10.0 out of 10, Exceptional, (2 reviews)
"On our 30th Anniversary trip to Vermont, New Hampshire and Maine we fell in love with Killington, Vermont. So much so we left the coast of Maine and last minute booked our remaining two nights back in Killington at the Poweder Run Lodge. The lodge was a wonderful experience! The location was beautiful, spacious, clean, had a fully stocked kitchen and spectacular views. The hosts were kind and easy to communicate with. We are older and need a continuous running fan and a little softer bed when we...
United States
Heidi P.
The price is AED 841
AED 2,745 total
includes taxes & fees
17 Nov - 18 Nov
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

12. The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi

The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi
The Woods
The price is AED 582
AED 1,355 total
includes taxes & fees
16 Nov - 17 Nov
The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi

13. Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
North Sherburne
10.0 out of 10, Exceptional, (1 review)
"Peak Hill, is a lovely and very clean home, with a fully stocked kitchen and comfy beds. This home is exactly as the pictures that are shown. We had a very small issue with the door lock (battery), called and it was fixed right away, wonderful service. The owner, Geri, we had the opportunity to meet and she is very kind and a pleasure to speak with. We travel alot and l bring pretty much my own kitchen, pillow...... with me where ever l go. However, l would of been fine using all at this...
United States
Essa R.
The price is AED 726
AED 2,577 total
includes taxes & fees
16 Nov - 17 Nov
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

14. Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Comfortable stay but there was some noise in the bigger bedroom from the heating panels so the sleep was disturbed. Other than this, we had a great time at the accommodation."
Canada
Smriti
The price is AED 686
AED 2,330 total
includes taxes & fees
16 Nov - 17 Nov
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace

15. Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.

Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
Killington
7.0 out of 10, Good, (6 reviews)
"Excellent brief stay."
United States
Ron L.
The price is AED 465
AED 1,903 total
includes taxes & fees
16 Nov - 17 Nov
Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.

16. Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington

Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington
Killington
9.0 out of 10, Wonderful, (7 reviews)
"Loved the quiet seclusion of the Shack, but also that we were close to hikes, lakes, markets, and food. We had a wonderful and relaxing stay!!"
United States
Sarah G.
The price is AED 664
AED 2,076 total
includes taxes & fees
16 Nov - 17 Nov
Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington

17. Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Relaxing Rutland Retreat Near Skiing, Dining & Hiking
Rutland
10.0 out of 10, Exceptional, (1 review)
The price is AED 1,377
AED 2,567 total
includes taxes & fees
16 Nov - 17 Nov
Relaxing Rutland Retreat Near Skiing, Dining & Hiking

18. 4BR Home | Walk Downtown Rutland + Trails

4BR Home | Walk Downtown Rutland + Trails
Rutland
10.0 out of 10, Exceptional, (8 reviews)
"House was clean, organized and spacious. Great location as well, close to grocery, gas and restaurants. Host answered questions quickly. "
United States
Dominic C.
The price is AED 661
AED 1,331 total
includes taxes & fees
16 Nov - 17 Nov
4BR Home | Walk Downtown Rutland + Trails

19. Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.

Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.
Rutland
9.4 out of 10, Exceptional, (6 reviews)
"Perfect spot for a large group to enjoy Rutland, Killington, and the surrounding area. Plenty of beds for everyone, and bathrooms so no one felt cramped whatsoever. Beautiful home and safe neighborhood. All around a great stay. If we come back for the US Open of MTB next year, this house would be high on our list to stay in again."
United States
Matthew T.
The price is AED 1,328
AED 3,565 total
includes taxes & fees
16 Nov - 17 Nov
Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.

20. Liquid Lodge Lower: 2BR Duplex near Killington with 1 PM Checkout

Liquid Lodge Lower: 2BR Duplex near Killington with 1 PM Checkout
Killington
The price is AED 708
AED 1,983 total
includes taxes & fees
16 Nov - 17 Nov
Liquid Lodge Lower: 2BR Duplex near Killington with 1 PM Checkout
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Learn more about Pittsford

Nestled in Vermont's Green Mountains, Pittsford offers hiking trails through New England forest and swimming at the historic Pittsford quarry during summer months. Visit the New England Maple Museum to learn about syrup production or explore nearby Rutland's downtown shops and restaurants.

A forest with a moss-covered rock and a stream.

Top reviews in Pittsford

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