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Top Holiday Rentals in Pittsford

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Interior
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, 451 reviews
"The cabin is beautiful and very cozy. I would definitely stay again in the future. Maxis is a great place to eat breakfast. If your planning to cook yourself make sure to get meat and anything else you want on the way as everything is at least 20 minutes or more drive."
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Cozy Loft for two with Hot Tub
Exterior
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, 200 reviews
"We couldn’t have asked for a better spot! The Little Loft was so clean and spotless and we really appreciated all the friendly tips and recommendations from the owner. The hot tub and fire pit were great-we used both every night. Our pup also loved his stay! 10/10!!"
Cozy Loft for two with Hot Tub
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Exterior
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, 179 reviews
"There was an issue at our check in that was quickly resolved and we enjoyed our stay a lot. Quiet, relaxing, and the area has some great restaurants. We stayed for our anniversary and will definitely will return."
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Ultimate relaxing vacation
Ultimate relaxing vacation
9.8 out of 10, Exceptional, 156 reviews
"Fantastic property, in a wonderful setting, with a terrific host."
Ultimate relaxing vacation
Private lake-front cabin with walk-in access to water, next to state park.
Smart TV, fireplace
Private lake-front cabin with walk-in access to water, next to state park.
9.8 out of 10, Exceptional, 42 reviews
"Dan is a great host, very accommodating. The cottage was very clean. It was perfect for our fishing trip. Plenty of room on the dock for 2 bass boats, power within 100 feet of dock. Between the 4 of us we landed over 120 fish during our 3 night stay. All catch and release. We would definitely stay here again!"
Private lake-front cabin with walk-in access to water, next to state park.
Charming, dog-friendly home with a private sauna, full kitchen, & furnished deck
Indoor pool
Charming, dog-friendly home with a private sauna, full kitchen, & furnished deck
9.6 out of 10, Exceptional, 53 reviews
"Everything was great, good location close to Killington and the house had everything we needed!"
Charming, dog-friendly home with a private sauna, full kitchen, & furnished deck
Killington Center Inn & Suites by Killington VR - Studios
Studio | Aerial view
Killington Center Inn & Suites by Killington VR - Studios
3.0 star property
10.0 out of 10, Exceptional, 1 review
"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
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Property grounds
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
9.8 out of 10, Exceptional, 29 reviews
"We had a great stay here! Looked just like the pictures. We especially loved the hot tub. Would love to come back."
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Quaint lakefront home with great views & full kitchen - dog-friendly
Property grounds
Quaint lakefront home with great views & full kitchen - dog-friendly
8.6 out of 10, Excellent, 19 reviews
"The cabin was pretty clean when we got there and it was a beautiful view."
Quaint lakefront home with great views & full kitchen - dog-friendly
Luxurious Secluded Cottage Massage Studio on Site
Fridge, microwave, oven, stovetop
Luxurious Secluded Cottage Massage Studio on Site
10.0 out of 10, Exceptional, 35 reviews
"David's place exceeded my expectations! Very smart design and layout. Quality craftmanship and attention to detail. Super clean. I wish my daughter and i could have stayed longer! Close enough to Middlebury College for this to be a great option for 2 people. David was very nice to stop by to introduce himself and see if we needed anything. We didn't see him again, but knew he was only a phone call away. Perfect."
The price is €196
per night
22 Jul - 23 Jul
Luxurious Secluded Cottage Massage Studio on Site
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
Indoor pool
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
8.8 out of 10, Excellent, 23 reviews
"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
Charming dog-friendly home with private deck, firepit, washer/dryer, & cable
Fridge, microwave, oven, stovetop
Charming dog-friendly home with private deck, firepit, washer/dryer, & cable
9.2 out of 10, Wonderful, 22 reviews
"We enjoyed our time and it was very close to Okemo Mountain"
Charming dog-friendly home with private deck, firepit, washer/dryer, & cable
Doc's Lake house 1st floor, 2 bedroom apartment
Exterior
Doc's Lake house 1st floor, 2 bedroom apartment
10.0 out of 10, Exceptional, 55 reviews
"We really enjoyed staying at this cozy, well-equipped lake house. Everything was available to make the stay an enjoyable one. The driveway entrance and property were cleared for our arrival following a significant snowstorm. Communicating with the owner was a pleasure, with every a phone call or text message answered. Who would’ve thought seeing the solar eclipse of 2024 would be so easy and exciting! It was the owner and accommodations that made it all possible for planning the trip. We truly...
Doc's Lake house 1st floor, 2 bedroom apartment
Views! Enjoy the Entire 3-floor Custom Chalet, AC+1gig internet on 18 acres.
Exterior
Views! Enjoy the Entire 3-floor Custom Chalet, AC+1gig internet on 18 acres.
9.8 out of 10, Exceptional, 93 reviews
"The chalet was great! Close by to lakes, and offered beautiful views!"
Views! Enjoy the Entire 3-floor Custom Chalet, AC+1gig internet on 18 acres.
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
Exterior
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
10.0 out of 10, Exceptional, 147 reviews
"Beautiful home and property with plenty of space for our extended family members to connect and yet have privacy for each couple as well. We will definitely return!"
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
Comfortable mountain gem with pool, mountain views, & indoor parking space
Property grounds
Comfortable mountain gem with pool, mountain views, & indoor parking space
8.8 out of 10, Excellent, 19 reviews
"The unit and building are showing their age, but everything is clean and the location is great. The kids enjoyed the brand new pool, sauna, and hot tub"
The price is €289
per night
3 Jul - 4 Jul
Comfortable mountain gem with pool, mountain views, & indoor parking space
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, 33 reviews
"Excellent quiet spot on the mountain. Beautiful town home. The house is closer to the trail than any of the lodges (about 20 feet). I was here on an abnormally hot day in the summer so I didn't ski or snowboard, but the AC came in handy and worked very well. Thanks for a great stay!"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Rustic Roxbury Ski Farmhouse with Trails!
Interior
Rustic Roxbury Ski Farmhouse with Trails!
9.6 out of 10, Exceptional, 4 reviews
"Overall a great experience. Owner was communicative and everything was as advertised."
Rustic Roxbury Ski Farmhouse with Trails!
edgemont 3 bedrooms wood fireplace updated baths ski home on shuttle sleeps 8
Exterior
edgemont 3 bedrooms wood fireplace updated baths ski home on shuttle sleeps 8
9.4 out of 10, Exceptional, 56 reviews
"We came into town to see our friend play a two night show at Pickle Barrel. The place was perfect. Check in info was thorough and easy. Kim was great. She was responsive to communications and very accommodating. Would definitely stay here or one of her other properties again!"
edgemont 3 bedrooms wood fireplace updated baths ski home on shuttle sleeps 8
The Swirl Suite at Killington: Brand New Remodeled 1 BR/2BA Suite 142
Aerial view
The Swirl Suite at Killington: Brand New Remodeled 1 BR/2BA Suite 142
10.0 out of 10, Exceptional, 7 reviews
"We loved the condo. We stayed for a school break, family of three and it was just what we needed to unplug from our busy life. Easy to get everywhere. We will definitely rent it again on our next trip."
The Swirl Suite at Killington: Brand New Remodeled 1 BR/2BA Suite 142
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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.

Other types of properties in Pittsford you may be interested in

Killington Mountain Lodge, Tapestry Collection by Hilton
Terrace/patio
Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 star property
7.4 out of 10, Good, 1,000 reviews
"Conveniently located near the mountain. Hilton did a good job updating the condition of the property. Breakfast should still be complimentary (not worth what they’re charging). "
The price is €148
per night
9 Jul - 10 Jul
Killington Mountain Lodge, Tapestry Collection by Hilton
Comfort Inn Trolley Square
Indoor pool
Comfort Inn Trolley Square
2.5 star property
8.0 out of 10, Very good, 1,004 reviews
"They are under major reconstruction. The pool was pretty nice. It seemed like the property needed updating. "
The price is €143
per night
30 Jun - 1 Jul
Comfort Inn Trolley Square
Middlebury Inn
Exterior
Middlebury Inn
3.0 star property
8.8 out of 10, Excellent, 1,003 reviews
"Lovely property right in beautiful downtown Middlebury. Staff were polite and knowledgeable. Restaurant was perfect for a quick bite. Loved it!"
The price is €163
per night
8 Jul - 9 Jul
Middlebury Inn
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.

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.

How many holiday rentals are there in Pittsford?

Expedia has 7 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.

Recent reviews of Pittsford properties
Expedia verified reviews

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

5/5 Excellent
"I had read some reports about people not liking the place because of ongoing renovations and the fact that their room was not clean. I found it was absolutely fine. Sure, they're renovating but I wasn't put into an unrenovated room (I can't imagine them doing that) and my room was clean, up-to-date, and comfortable."
A verified traveller stayed at Days Inn by Wyndham Rutland/Killington Area
Posted 2 days ago
Days Inn by Wyndham Rutland/Killington Area