Pittsford Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Pittsford vacation rentals

A modern kitchen with a dishwasher, a coffee maker, and a dining area with a wooden table set for two.

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 CA $124
CA $232 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Rutland Retreat
A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

2. 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 CA $125
CA $294 total
includes taxes & fees
Nov 8 - Nov 9
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A modern bedroom with a bed, bedside table, and a window with a view.

3. The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
Killington
9.6 out of 10, Exceptional, (5 reviews)
"Place was great"
United States
Nathan H.
The price is CA $108
CA $363 total
includes taxes & fees
Nov 8 - Nov 9
The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
A kitchen with granite countertops, wooden cabinets, and a built-in oven.

4. The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Mendon
9.6 out of 10, Exceptional, (22 reviews)
"The communication with Host was awesome to a question we had; Dave's response was so helpful. Beautiful place, quiet. Get ‘get-away’."
United States
Diane
The price is CA $207
CA $605 total
includes taxes & fees
Nov 8 - Nov 9
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
A swimming pool with a hot tub, surrounded by a building with balconies and a fenced area with trees.

5. Mountain Green ground-floor condo with private yard off the patio

Mountain Green ground-floor condo with private yard off the patio
Killington
The price is CA $115
CA $391 total
includes taxes & fees
Nov 8 - Nov 9
Mountain Green ground-floor condo with private yard off the patio
A modern living room with a glass coffee table, a sofa, a TV mounted on the wall, a fireplace, and a blue accent wall.

6. Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
Killington
9.6 out of 10, Exceptional, (5 reviews)
"Great room!"
United States
Carla M.
The price is CA $106
CA $361 total
includes taxes & fees
Nov 8 - Nov 9
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
An aerial view of a residential area with houses, a swimming pool, and a parking lot.

7. Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
Killington
9.4 out of 10, Exceptional, (10 reviews)
"Beautiful place . My sister was visiting USA/ Vermont for the first time . We went to the Breakfast cafe next door it was amazing . "
United States
Asad B.
The price is CA $135
CA $370 total
includes taxes & fees
Nov 8 - Nov 9
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
A bedroom with two beds, a dresser, a window with a view of greenery, and a painting on the wall.

8. Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631

Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631
Killington
9.0 out of 10, Wonderful, (7 reviews)
"Easy, convenient location. Perfect no frills last minute ski trip. Would stay again. Good communication."
United States
Marcus G.
The price is CA $109
CA $370 total
includes taxes & fees
Nov 9 - Nov 10
Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631
A living room with a sofa, a dining table with chairs, a kitchen area with wooden cabinets, and a bar.

9. Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
Killington
9.8 out of 10, Exceptional, (14 reviews)
"We had such a great time staying here. It was clean, cozy and so convenient to walk right out the door to the slopes! "
United States
Susanne B.
The price is CA $168
CA $445 total
includes taxes & fees
Nov 8 - Nov 9
Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
A kitchen with a large island, wooden ceiling beams, and various kitchen appliances.

10. Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Leicester
10.0 out of 10, Exceptional, (97 reviews)
"The cottage was just lovely. Very comfortable. And the host was really nice and helpful. A wonderful stay!"
United States
Laura Ann
The price is CA $186
CA $277 total
includes taxes & fees
Nov 22 - Nov 23
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
A two-story building with a dark brown exterior, a covered porch, and a number '303' sign.

11. Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings

Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings
North Sherburne
8.0 out of 10, Very good, (17 reviews)
"We had a great time!"
United States
Matthew R.
The price is CA $139
CA $510 total
includes taxes & fees
Nov 7 - Nov 8
Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings
A yurt with a red door, a visible interior with a fire, and snow outside.

12. Off-Grid Mongolian Yurt on Vermont Sheep Farm

Off-Grid Mongolian Yurt on Vermont Sheep Farm
Poultney
The price is CA $168
CA $239 total
includes taxes & fees
Nov 9 - Nov 10
Off-Grid Mongolian Yurt on Vermont Sheep Farm
A ski resort with multiple buildings, a ski slope, and a mountain in the background.

13. Jack S`Bearo - Slopes, Fireplace, Pool

Jack S`Bearo - Slopes, Fireplace, Pool
Killington
10.0 out of 10, Exceptional, (17 reviews)
"Great condo and building. Everything in excellent condition. Convenient location."
United States
Joseph S.
The price is CA $187
CA $358 total
includes taxes & fees
Nov 8 - Nov 9
Jack S`Bearo - Slopes, Fireplace, Pool
A living room with a wooden console table, a potted plant, and two clocks. A staircase and a fireplace with a TV are in the background.

14. 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 CA $198
CA $758 total
includes taxes & fees
Nov 8 - Nov 9
Ski Home/Arcade Mountain Views Near Killington/Woodstock
A modern kitchen with stainless steel appliances, wooden flooring, and white cabinetry.

15. Rutland apartment on the bus route with central A/C, near Pico

Rutland apartment on the bus route with central A/C, near Pico
Rutland
8.0 out of 10, Very good, (1 review)
"Spotless interior, but the exterior will benifit from a refresh.Conveniently walkable for shops and restaurants."
United States
Thomas A.
The price is CA $206
CA $467 total
includes taxes & fees
Nov 10 - Nov 11
Rutland apartment on the bus route with central A/C, near Pico
A modern kitchen with white cabinets, a built-in microwave, and a stainless steel refrigerator.

16. The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.

The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.
Killington
9.2 out of 10, Wonderful, (10 reviews)
"Perfect clean space, very comfortable and great location for the week. We were not big fans of the mattress toppers, they kept sliding off, but that is a personal preference matter. Staff communication was 10 out of 10. Highly recommend."
United States
Lisa
The price is CA $167
CA $565 total
includes taxes & fees
Nov 8 - Nov 9
The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.
A modern living room with a stone fireplace, a flat-screen TV mounted above it, wooden flooring, and a kitchen area in the background.

17. Modern Killington Farmhouse Condo: Close to it all! 412

Modern Killington Farmhouse Condo: Close to it all! 412
Killington
10.0 out of 10, Exceptional, (62 reviews)
"Fantastic spot for hitting mountains as a family. Incredibly clean, convenience, and comfortable. Couldn’t be better! EV charging on site was the icing on the cake "
United States
Tyler L.
The price is CA $168
CA $529 total
includes taxes & fees
Nov 8 - Nov 9
Modern Killington Farmhouse Condo: Close to it all! 412
A modern loft bedroom with a sloped ceiling, a fireplace, a large TV, and a balcony with a scenic view.

18. Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.

Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.
Killington
10.0 out of 10, Exceptional, (15 reviews)
"A wonderful up to date property a short walk to the lifts! Would definitely stay here again."
United States
Mike B.
The price is CA $153
CA $446 total
includes taxes & fees
Nov 8 - Nov 9
Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.
A living room with a fireplace, a sofa, a coffee table, and a television.

19. Mountain Green high-floor front condo in Building 3 with ski trail views

Mountain Green high-floor front condo in Building 3 with ski trail views
Killington
8.8 out of 10, Excellent, (47 reviews)
"Great location. Great amenities. Great communication. "
United States
Jason B.
The price is CA $147
CA $509 total
includes taxes & fees
Nov 8 - Nov 9
Mountain Green high-floor front condo in Building 3 with ski trail views
A two-story house with a covered porch and a gabled roof.

20. 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)
"Very clean and comfortable. Would definitely rent again!"
United States
Molly T.
The price is CA $189
CA $385 total
includes taxes & fees
Nov 8 - Nov 9
Historic Victorian Estate 4 Bed 2 Bath Fast Wifi
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.
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Top Pittsford Hotel Reviews

A modern interior with a wooden reception desk, seating area, and large windows.
Hampton Inn Rutland

Hampton Inn Rutland

Hampton Inn Rutland
Rutland

10/10 Excellent

Room was very clean and beds comfortable.
Canada
shelly-lynn
Reviewed November 13, 2025
Hampton Inn Rutland

Find out more about Pittsford

Everything you need to know about Pittsford vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsford vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pittsford vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pittsford vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pittsford. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pittsford vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pittsford vacation rentals we have selected for you start as low as CA $107 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pittsford rentals

At Expedia, we put the best Pittsford vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pittsford rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pittsford vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pittsford. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find a vacation rental in Pittsford?

Yes, there are vacation rentals close to well known points of interest in Pittsford, or you can select a more remote option if you want a relaxing place to stay. Pittsford is known for its ski areas and shopping. Make sure you have time to check out the restaurants and museums during your trip.

What are some of the best vacation home rentals in Pittsford?

Rustic home with a private hot tub, cable, & washer/dryer: This vacation home rental outside of Pittsford is located in the city center and has a fireplace, a hot tub, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in Pittsford?

Cultural attractions include New England Maple Museum, whereas Green Mountain National Forest is a spot to enjoy nature. In the larger area, you’ll find Proctor-Pittsford Country Club and Taconic Mountains Ramble State Park.

What’s a vacation rental in Pittsford like?

Vacation rentals are private properties you can book for a short or long stay in Pittsford. Vacation rentals feature extras such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for family trips or small group gatherings.