Pittsford Holiday Rentals

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Holiday Rentals in Pittsford

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (39)
"Amazing house great price but note that there are only two split units cooling down the house which means one bed room only gets ac if the other bedrooms split unit is on and both doors are open"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

10.0 out of 10, Exceptional, (473)
"The cabin was amazing, the design and decor is perfect and the space is perfect. The hot tub and fire pit were so lovely in the evening, and the movie theatre was also excellent for watching TV and films. Jeff was an excellent host, super friendly and helpful and the area was lovely and quiet, very peaceful. Thanks again! "
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

Cozy Loft for two with Hot Tub

10.0 out of 10, Exceptional, (220)
"The Cozy Loft was the perfect place to get away from everyday work and left stressors. It provided us a place to rest and relax. It was also not far from towns to explore (great hiking, restaurants, antique shopping). Would highly recommend to others traveling to that area. "
Cozy Loft for two with Hot Tub

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (196)
"It was a wonderful little cabin that was clean and decorated comfortably. It had everything we needed. The hot tub was delightful! "
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Ultimate relaxing vacation

9.8 out of 10, Exceptional, (176)
"Right on a quiet lake - so peaceful and nice. Great back porch and a dock at the shoreline. Nice big open layout had a great feel to it. I was there alone but it would be outstanding for a group that likes to sit outside and have a fire and make the most of the scenery."
The price is AU$278
includes taxes & fees
18 Dec - 19 Dec
Ultimate relaxing vacation

Ski-in/ski-out condo with W/D, indoor pool, & hot tub

9.0 out of 10, Wonderful, (18)
"We loved the condo and the easy walking avvess to all of what Killington offers! We would definitely stay here again! "
Ski-in/ski-out condo with W/D, indoor pool, & hot tub

Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

8.8 out of 10, Excellent, (39)
"Accurate representation of the property. Check in was easy after some confusion as the access door is right next to another unit and not wanting to interfere with another group late at night. Owners were able to clarify and said they would put a better note into the welcome message to alleviate future confusion. Overall, good price and would stay again."
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

Beautiful 4-Bedroom Home beside Middlebury College

9.8 out of 10, Exceptional, (41)
"Great place and location!"
Beautiful 4-Bedroom Home beside Middlebury College

Trail Creek 33 | Condo in Killington

9.8 out of 10, Exceptional, (20)
"The location of the property was great.. Centrally located to everything we wanted to see. I would have liked to have a vacuum or even a broom available. The place had a few areas that could have been cleaner. "
Trail Creek 33 | Condo in Killington

Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.

10.0 out of 10, Exceptional, (159)
"Quiet getaway for the weekend just the two of us. It was the perfect spot. Out of the busy but a quick drive to get something to eat when you get hungry. The drive wasn’t bad either. Deb and Angelo were amazing to communicate with also. "
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

10.0 out of 10, Exceptional, (48)
"Our stay at Camp Tiger Ted was so wonderful. The amount of detail and care David put into building and now maintaining the property is second to none. The house was meticulously clean and had so many charming details. David also gave us both massages in his in home studio which waA the most relaxing way to end our stay!"
The price is AU$304
includes taxes & fees
1 Dec - 2 Dec
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

8.4 out of 10, Very good, (25)
"We were a bit disappointed with this property. The pictures are a bit misleading as it felt dark and stuffy, which we didn’t expect. There was a strong cigarette odor that was hard to adjust to and the room kept dropping down to very cold temperatures (50s) even after we adjusted the thermostat. This was stressful since we have a 15 month old and were worried about her being too cold all night. The deck was completely blocked by a mound of treacherous ice from water dripping off the roof, which...
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Dog-friendly lake escape with sunroom, high-speed WiFi, water views & central AC

9.4 out of 10, Exceptional, (25)
"Beautiful property with amazing view of the lake the directions were a little off according to the website but we found it very enjoyable and relaxing stay"
Dog-friendly lake escape with sunroom, high-speed WiFi, water views & central AC

Dog-friendly cabin with forest setting, woodstove & deck - near Killington

8.8 out of 10, Excellent, (18)
"Very cute cabin in the woods. Less than 2 miles off of route 4, which made it easy to get anywhere in Vermont!"
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

9.8 out of 10, Exceptional, (18)
"Gorgeous property with everything that we needed! It was relaxing and comfortable for everyone. The kids had a blast! The property management team was great with communication and offered early check in and late check out. Would absolutely stay here again!"
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

9.8 out of 10, Exceptional, (30)
"We had a lovely time at the Arched Chalet for my family's annual vacation in Vermont. It was very comfortable, well-appointed, and in a great location. Even in the summer heat we did not need the AC - it was so comfortable with the fans and the lower level is naturally cool. Great location near Camp Plymouth (we went to the lake twice), and restaurants/shops in Ludlow and Woodstock."
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

Charming, dog-friendly home with a private sauna, full kitchen, & furnished deck

9.6 out of 10, Exceptional, (61)
"Place seemed older/dated, no a/c, my daugther's commented they heard scratching in the walls at night so may have been some type of rodent. Pots and pans were old and rough to cook with. "
Charming, dog-friendly home with a private sauna, full kitchen, & furnished deck

Mountain Green Resort with Free WiFi and Full Kitchen — Walk to Slopes

8.8 out of 10, Excellent, (13)
"The property was exactly as advertised and clean. The pool was open and it was a good option to relax. The acces to parking was terrible - muddy, sandy, icy gravel. It is clear that nobody was thinking about this at all. The access to lifts was not ski in/out, but shuttle was great, and running all time! There was a ski locker, which was convenient, though nobody told us about it and we figured it out ourselves. Card for pool did not work but the office was open and provided the correct one,...
The price is AU$569
includes taxes & fees
25 Nov - 26 Nov
Mountain Green Resort with Free WiFi and Full Kitchen — Walk to Slopes

Relax by "The Water's Edge" & enjoy amazing views and year round fun! 6BR/3.5BA

10.0 out of 10, Exceptional, (6)
"I booked this house based primarily on its location (easy access to a lake/hikes); size (we needed lots of room for 10 people); and availability. This fit our requirements, and when we got there, exceeded our expectations. Our family loved everything about the home and property from its location in a quiet lakeside community to its décor and spaciousness and all the amenities inside or outside. The location is central to some nice hikes. Crystal Beach is just around the corner, literally. The...
Relax by "The Water's Edge" & enjoy amazing views and year round fun! 6BR/3.5BA

Killington Center Inn & Suites by Killington VR - Studios

3.0 star property
10.0 out of 10, Exceptional, (1)
"We loved our little unit. Everything was clean and very modern. We especially loved the electric fireplace. Would stay here again. "
Killington Center Inn & Suites by Killington VR - Studios
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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Other types of properties in Pittsford you may be interested in

Comfort Inn Rutland - Killington

2.5 star property
8.0 out of 10, Very good, (1002)
"Staff helpful and friendly. Rooms small, but space is used efficiently. Rooms were clean and welcoming. There is occasional noise from the mechanics of the building (e.g. HVAC). A bit outside of town, probably a 20 minute walk to city center. I was comfortable, felt safe, and would stay there again if in the area."
The price is AU$175
includes taxes & fees
8 Dec - 9 Dec
Comfort Inn Rutland - Killington

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 star property
7.2 out of 10, Good, (1000)
"Great experience! It was a lot of fun around the pool table or the fire pit outside. We loved it! It was great to have our dog with us everywhere around the hotel. Everything is very clean and in modern design. The only downside was that the restaurant dinner menu is limited to 5 options and there is no breakfast, just a Starbucks kiosk with coffee and muffins. We will go back! "
The price is AU$273
includes taxes & fees
9 Dec - 10 Dec
Killington Mountain Lodge, Tapestry Collection by Hilton

Days Inn by Wyndham Rutland/Killington Area

2.5 star property
6.4 out of 10, (1000)
"Said just renovated but kept old tub"
The price is AU$189
includes taxes & fees
24 Nov - 25 Nov
Days Inn by Wyndham Rutland/Killington Area
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.
Beautiful view of the beach with palm trees

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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?

4 Season Secluded Lakefront Home near Ski Mountains : This holiday home rental outside of Pittsford is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of books.

How many holiday rentals are there in Pittsford?

Expedia has 4 holiday rentals for your stay in Pittsford.

What can I see and do in Pittsford?

While exploring the area, visit family-friendly sights like Pond Hill Ranch and Pro Rodeo, or get outside and enjoy nature at Lake Bomoseen. New England Maple Museum and Proctor-Pittsford Country Club are other places to visit while you're in town.

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.