Pittsford Vacation Rentals

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Vacation Rentals in Pittsford

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (47)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (256)
"Very happy with this little cabin. Communication with host was excellent. "
Cozy Loft for two with Hot Tub & Mtn Views

Ultimate relaxing vacation

9.8 out of 10, Exceptional, (198)
"The cottage was so cozy and comfy."
The price is CA $192
CA $246 total
includes taxes & fees
Sep 10 - Sep 11
Ultimate relaxing vacation

Mountain Green

2.0 star property
6.6 out of 10, (10)
"The condo was very cozy for a family of four and suited us perfectly. Beds were comfortable and condo was clean. "
The price is CA $219
CA $294 total
includes taxes & fees
Sep 2 - Sep 3
Mountain Green

Water front home with large two tiered deck! 2 bathrooms 😂

9.4 out of 10, Exceptional, (105)
"My family has stayed here 2 weekends and it was perfect for us. Great location and perfect area to relax. Our dog enjoyed swimming and we enjoyed fishing. Great communication with manager also. Look forward to staying here again!"
Water front home with large two tiered deck! 2 bathrooms 😂

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

10.0 out of 10, Exceptional, (509)
"Our stay at the Vermont Cabin "Romantic Retreat" was amazing. Owner was very communicative and made our stay stress free. Even though it's listed as a romantic retreat, it was great for the family too. The cabin was well stocked with everything we needed during our stay and the hottub was definitely a hit. We cant wait for our next stay."
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

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

9.0 out of 10, Wonderful, (54)
"Cozy but all the amenities, great location"
The price is CA $117
CA $234 total
includes taxes & fees
Sep 1 - Sep 2
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

Killington Retreat

2.0 star property
9.6 out of 10, Exceptional, (11)
"Had a great time staying so close to Killington. Sauna, hot tub and pool were a great way to warm up after a day of skiing."
Killington Retreat

Apt 2A Lake Bomoseen Inn “The Dog” with boat slip.

9.6 out of 10, Exceptional, (14)
"Nice property, close to friends and the Lake!"
Apt 2A Lake Bomoseen Inn “The Dog” with boat slip.

Classic Vermont Cabin on 2.5 acres Lake Frontage

9.8 out of 10, Exceptional, (114)
"Very quiet, well appointed cottage! So peaceful, beautiful scenery and VERY accommodating host!"
Classic Vermont Cabin on 2.5 acres Lake Frontage

Cottage on east side of Lake Bomoseen, on-site boat slip included

9.4 out of 10, Exceptional, (13)
"We enjoyed out stay here and will be coming back."
Cottage on east side of Lake Bomoseen, on-site boat slip included

Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub

3.0 star property
9.6 out of 10, Exceptional, (12)
"Very nice townhouse."
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub

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

8.0 out of 10, Very good, (35)
"Convenient for skiing and visiting the greater VT area. Unit has what you need for your stay."
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

10.0 out of 10, Exceptional, (56)
"It was such a lovely stay. Everything was super tidy, clean, comfortable and cozy. We especially loved reading about the story of the build. Would absolutely recommend! "
The price is CA $192
CA $295 total
includes taxes & fees
Sep 2 - Sep 3
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Trail Creek 75 | Condo in Killington

9.8 out of 10, Exceptional, (16)
"Having six in this place was tight, but we enjoyed our time. "
Trail Creek 75 | Condo in Killington

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (217)
"Cozy and scenic property here with more than enough space, great spot with a dog, to go hiking, or just relax."
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Vermont Lake House

10.0 out of 10, Exceptional, (22)
"Host was great and it was in a great location "
Vermont Lake House

Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

10.0 out of 10, Exceptional, (110)
"Nice rental for our family and the owner was very rsponsive."
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

Totally remodeled year round LAKEFRONT home with stunning views of Lake Bomoseen

10.0 out of 10, Exceptional, (40)
"Our granddaughter was getting married at Lake Bomoseen, only a short 3 or 4 minute ride from this beautiful house. We had our 4 grandchildren and their parents with us, this house let us spread out and have fun. We did not have good weather but that didn't stop my 8 year old granddaughter from jumping in the lake. We wish we could have enjoyed the outside more, but with a rainy weekend, we were so happy we had the expanse of this home. We played charades, games, made puzzles. This home has...
Totally remodeled year round LAKEFRONT home with stunning views of Lake Bomoseen

Glamping hut with WiFi in Ripton, biking, hiking, skiing

The price is CA $122
CA $229 total
includes taxes & fees
Sep 7 - Sep 8
Glamping hut with WiFi in Ripton, biking, hiking, skiing
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

Find out more about Pittsford

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 $117 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?

Water front home with large two tiered deck! 2 bathrooms 😂: This vacation home rental outside of Pittsford is located on a lake and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 larger area, you’ll find Proctor-Pittsford Country Club and Rutland Country Club.

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.