A sign for the Green Mountain National Forest Observation Site in Texas Falls.

Pittsford Holiday Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Pittsford holiday rentals

A modern kitchen with stainless steel appliances, wooden flooring, and white cabinetry.

1. Centrally located apartment for the skier & outdoor enthusiast

Centrally located apartment for the skier & outdoor enthusiast
Rutland
The price is AU$452
includes taxes & fees
3 Sept - 4 Sept
Centrally located apartment for the skier & outdoor enthusiast

2. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (16 reviews)
"The location was perfect, the property is very well maintained and comfortable. I would highly recommend this place!"
United States
Valerie
The price is AU$243
includes taxes & fees
14 Sept - 15 Sept
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.

3. 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
9.8 out of 10, Exceptional, (6 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 AU$326
includes taxes & fees
7 Sept - 8 Sept
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A kitchen with a large island, wooden ceiling beams, and various kitchen appliances.

4. 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, (89 reviews)
"Definitely super SUPER clean all throughout! The ambiance is perfect, just a beautiful cottage with all the amenities you might need. Perfect place to stay."
United States
Julian V.
The price is AU$300
includes taxes & fees
1 Sept - 2 Sept
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
A bedroom with a large bed, a TV mounted on the wall, and a sliding door leading to a bathroom.

5. Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Killington
10.0 out of 10, Exceptional, (16 reviews)
"Great condo and building. Everything in excellent condition. Convenient location."
United States
Joseph S.
The price is AU$376
includes taxes & fees
1 Sept - 2 Sept
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
A snow-covered residential area with multi-story buildings, a ski slope in the background, and a clear sky.

6. Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (29 reviews)
"The property is under major construction which was not disclosed when booking. The management fee was almost as much as the room rate, clearer description at time of booking would be appreciated."
United States
Keith
The price is AU$322
includes taxes & fees
8 Sept - 9 Sept
Mountain Green
A snow-covered outdoor area with a large arch structure, rocks, and a building in the background.

7. CubsCorner - Pool, Sauna, Gym, Close to Mountain!

CubsCorner - Pool, Sauna, Gym, Close to Mountain!
Killington
10.0 out of 10, Exceptional, (6 reviews)
"Great location with access to both Pico and Killington Mountains!"
United States
Olaf G.
The price is AU$623
includes taxes & fees
2 Sept - 3 Sept
CubsCorner - Pool, Sauna, Gym, Close to Mountain!
An aerial view of a residential area with houses, a swimming pool, and a parking lot.

8. 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, (8 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 AU$364
includes taxes & fees
1 Sept - 2 Sept
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
A spacious living room with wooden floors, a high ceiling with exposed beams, a dining area with a table and chairs, and large windows offering a view of the outdoors.

9. Killington Retreat | Deck-Fire Pit-Mountain Views!

Killington Retreat | Deck-Fire Pit-Mountain Views!
Clarendon
9.2 out of 10, Wonderful, (5 reviews)
"The living area is bigger than we expected, and we loved watching the horses next door. It's a short drive to downtown Rutland, and it's quiet. "
United States
Ahmad H.
The price is AU$525
includes taxes & fees
20 Sept - 21 Sept
Killington Retreat | Deck-Fire Pit-Mountain Views!
A spacious living area with a red sectional sofa, a wooden dining table, and a kitchen in the background.

10. 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 AU$889
includes taxes & fees
1 Sept - 2 Sept
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
A cozy living room with a brick fireplace, two sofas, a coffee table, and a TV mounted on the wall.

11. Killington condo 5 min to killington resort

Killington condo 5 min to killington resort
Killington
9.4 out of 10, Exceptional, (9 reviews)
"Great location!!"
United States
Nicholas C.
The price is AU$531
includes taxes & fees
1 Sept - 2 Sept
Killington condo 5 min to killington resort
A residential area with houses, a swimming pool, and a mountain backdrop.

12. 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, (4 reviews)
"Place was great"
United States
Nathan H.
The price is AU$362
includes taxes & fees
2 Sept - 3 Sept
The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
A rustic cabin with a wooden porch, a door, and a large potted plant.

13. Unique family-friendly Vermont cabin!

Unique family-friendly Vermont cabin!
Fair Haven
10.0 out of 10, Exceptional, (24 reviews)
"Staff was exceptional, atmosphere was inviting and overall property was great Loved the history of the Inn & craftsmanship/architecture of the building. We would absolutely stay again if we are ever in the area!"
United States
Jen C.
The price is AU$409
includes taxes & fees
2 Sept - 3 Sept
Unique family-friendly Vermont cabin!
An outdoor patio with a sofa, a patterned rug, and a lamp.

14. Cozy 1BR/1BA Mt Green Condo with Amenities and Discounted Ski Rentals. Shuttle.

Cozy 1BR/1BA Mt Green Condo with Amenities and Discounted Ski Rentals. Shuttle.
Killington
10.0 out of 10, Exceptional, (2 reviews)
"I would highly recommend a stay at this cozy Mt Green Condo. It was clean, spacious, had everything we needed, and was only a five minute shuttle ride to the mountain. The indoor pool and hot tub in the building were great to come back to after a full day of skiing. Thank you to Dave and the Simple Vacations Rental Team for a great few days away!"
United States
Erin M.
The price is AU$514
includes taxes & fees
1 Sept - 2 Sept
Cozy 1BR/1BA Mt Green Condo with Amenities and Discounted Ski Rentals. Shuttle.
An aerial view of a residential area with houses, a swimming pool, and a lake surrounded by forested hills.

15. Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441

Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441
Killington
8.0 out of 10, Very good, (1 review)
Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441
A spacious kitchen with a large island, wooden dining table, and chairs. There are multiple windows providing natural light and views of the outdoors.

16. 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, (5 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is AU$649
includes taxes & fees
6 Sept - 7 Sept
large ski ranch hot tub close to killington pets ok
A modern living room with a stone fireplace, a large TV mounted on the wall, and a wooden bench.

17. Killington Center Inn & Suites by Killington VR - 1 Bedrooms

Killington Center Inn & Suites by Killington VR - 1 Bedrooms
3.0 star property
Killington
2.0 out of 10, (1 review)
"This place does not have clean water. The water that comes from the faucets is brown and there are notices on the doors about high levels of carcinogens. "
United States
Tyler
Killington Center Inn & Suites by Killington VR - 1 Bedrooms
A modern living room with a red sectional sofa, a round coffee table, wooden ceiling beams, a kitchen area, and a balcony with a view of trees.

18. 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
The price is AU$877
includes taxes & fees
1 Sept - 2 Sept
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
A living room with a fireplace, a sofa, a coffee table, and a television.

19. Resort condo with mountain views, full kitchen, and free WiFi

Resort condo with mountain views, full kitchen, and free WiFi
Killington
8.8 out of 10, Excellent, (47 reviews)
"Great location. Great amenities. Great communication. "
United States
Jason B.
The price is AU$512
includes taxes & fees
13 Sept - 14 Sept
Resort condo with mountain views, full kitchen, and free WiFi
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.

20. 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 AU$765
includes taxes & fees
1 Sept - 2 Sept
Ski Home/Arcade Mountain Views Near Killington/Woodstock
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

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent
"Our room was very clean, bed sheets perfect, 3 pillows per bed (2 double beds), only thing a little bothering was the lack of pressure in the shower and the sink... but sufficient for my needs. Air conditionning was off when we came in but after a few minutes, the room was confortable, so very efficient A/C. I was surprised of the included continental breakfast, very complete with self-made waffles and 3 kinds of cereals, yogurt, toasts, bagels, muffins, pastries... coffee of course, tea, 4 different juices... I will return for shure."
Eric 1-night trip
Posted 16 hours ago
Days Inn by Wyndham Rutland/Killington Area

Find out more about Pittsford

Everything you need to know about Pittsford holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsford holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Pittsford holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pittsford holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pittsford holiday rentals we have selected for you start as low as AU$300 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Pittsford rentals

At Expedia, we put the best Pittsford holiday 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 holiday.

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 holiday rental in Pittsford?

Yes, there are holiday rentals close to the most popular sights in Pittsford, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Pittsford has to offer?

Water front home with large two tiered deck! 2 bathrooms 😂: This holiday home rental outside of Pittsford is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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 wider area, you’ll find Proctor-Pittsford Country Club and Wilson Castle.

What’s a holiday rental in Pittsford like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pittsford. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for small groups.