Pittsford holiday homes

We found 884 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Pittsford to find one that's perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a washer and dryer. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Pittsford

Showing deals for:4 Dec - 11 Dec

Imagine having mountain trail views while playing bartender!
Welcome to the Highline Lodge!
The great room features your own private bar, gas fireplace, and cozy seating!
Mix up some drinks for your party at the 9 seat bar with 65" smart TV!
Exceptional
(68 reviews)

Rent An Entire Inn! Sleeps 30! As seen on Staycation TV!

Killington

8% off
NZ$27,492
for 7 nights, 1 room
NZ$3,927 per night
includes taxes & fees
Rent An Entire Inn! Sleeps 30! As seen on Staycation TV!
Main Lodge Dining--Tables extend out so 20 people can sit & eat comfortably
Spring at Killington Big House
Main Lodge Great Room seats 17 without additional chairs
Holidays at the Big House are extra special!!  Invite the whole family!
Exceptional
(144 reviews)

Killington Big House: Largest Vacation Rental in Killington

Killington

8% off
NZ$17,932
for 7 nights, 1 home
NZ$2,562 per night
includes taxes & fees
Killington Big House: Largest Vacation Rental in Killington
Private kitchen
Sun Room
Dining
Living area
Exceptional
(11 reviews)

Luxury 4 Bedroom Ski Retreat Near Killington, Pico & Mountain Top Inn.

Rutland

8% off
NZ$9,067
for 7 nights, 1 home
NZ$1,295 per night
includes taxes & fees
Luxury 4 Bedroom Ski Retreat Near Killington, Pico & Mountain Top Inn.
Sit down for coffee beside the window, with the front door and living room nearby.
Prep, rinse, and cook without crossing the room for the essentials.
The kitchen pass-through opens toward the dining table and fireside living room.
Wide windows bring daylight into the shared living and dining space.
Exceptional
(18 reviews)

Entire Killington Cabin Duplex: 8BR, Two Kitchens and Hot Tub

Killington

8% off
NZ$20,238
for 7 nights, 1 cabin
NZ$2,891 per night
includes taxes & fees
Entire Killington Cabin Duplex: 8BR, Two Kitchens and Hot Tub
Wood railings and carpeted steps carry the cabin's warm finish into the stairway.
Pass plates and drinks through the counter opening without missing what is happening in the living room.
Snowy woods frame the deck hot tub on cold winter days.
Meals and conversation flow easily between the dining table and the adjoining living room.
Exceptional
(65 reviews)

Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape

Killington

7% off
NZ$9,221
for 7 nights, 1 cabin
NZ$1,317 per night
includes taxes & fees
Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape
Dining
Terrace/patio
Private kitchen
Exterior
Exceptional
(96 reviews)

5 BR 3.5 Bath Killington Home with Hot Tub, Huge Dining Table, Summer Pool

Killington

8% off
NZ$11,494
for 7 nights, 1 home
NZ$1,642 per night
includes taxes & fees
5 BR 3.5 Bath Killington Home with Hot Tub, Huge Dining Table, Summer Pool
Drone shot showing our home and its wooded privacy.
Our signature fieldstone fireplace in our huge great room.
Our fully-equipped kitchen.
Awesome sectional couch around which to gather.
Exceptional
(20 reviews)

4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!

Killington

15% off
NZ$6,202
for 7 nights, 1 chalet
NZ$886 per night
includes taxes & fees
4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!
Interior
Breathtaking views
Winter Views
Wrap around deck with a grill and outdoor furniture
Wonderful
(23 reviews)

Luxury 7BR/7BA Mountain Retreat with Sauna, Hot Tub, and Stunning Views

Rutland

12% off
NZ$18,431
for 7 nights, 1 home
NZ$2,633 per night
includes taxes & fees
Luxury 7BR/7BA Mountain Retreat with Sauna, Hot Tub, and Stunning Views
Tall windows bring wooded views and daylight into the main gathering space.
Settle into the sectional for a movie or gather by the brick fireplace for a night in.
The covered porch shelters the front door and provides a clear, well-lit arrival.
The central hall links the kitchen and dining area with the staircase to the upper floor.
Exceptional
(23 reviews)

4BR Killington Home Perfect for Families, Pet-Friendly

Killington

7% off
NZ$9,432
for 7 nights, 1 home
NZ$1,347 per night
includes taxes & fees
4BR Killington Home Perfect for Families, Pet-Friendly
Living Room
Living room
Interior
view from the Foundry
Exceptional
(61 reviews)

Private Mountain View minutes to Hiking, biking, golfing, skiing, snowboarding

Killington

8% off
NZ$13,138
for 7 nights, 1 home
NZ$1,877 per night
includes taxes & fees
Private Mountain View minutes to Hiking, biking, golfing, skiing, snowboarding
Cook and eat together in a bright kitchen with the dining table beside the windows.
The pass-through leaves the living room in view while you prepare food in the kitchen.
A wide driveway leads to the detached garage beside the cottage.
Gather on the sectional while the wide front window looks out toward the porch and yard.
Exceptional
(21 reviews)

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

Rutland

7% off
NZ$3,537
for 7 nights, 1 cottage
NZ$505 per night
includes taxes & fees
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Long lunches and evening meals stay sheltered on the broad deck overlooking the lawn.
The forest-framed exterior shows off the broad decks and covered hot tub before you step inside.
Rain or shine, the covered hot tub is ready for a quiet soak among the trees.
The sectional and couch give everyone a comfortable place to gather for movie night or conversation.
Exceptional
(70 reviews)

25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

Killington

7% off
NZ$9,506
for 7 nights, 1 home
NZ$1,358 per night
includes taxes & fees
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
Dining
Interior
Living area
Terrace/patio
Exceptional
(9 reviews)

5 Min to Lodges & Town; Arcade & Ping Pong Table; Hot Tub; Renovated

Killington

7% off
NZ$12,298
for 7 nights, 1 home
NZ$1,757 per night
includes taxes & fees
5 Min to Lodges & Town; Arcade & Ping Pong Table; Hot Tub; Renovated
Come in through the bright entry and step directly into the open living and dining spaces.
Pull up a stool at the island for breakfast, snacks, or company while someone cooks.
From the island, the open dining room is in view and ready for everything from breakfast to dinner.
Gather on the sectional for a movie or an evening by the fireplace.
Exceptional
(6 reviews)

Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.

Rutland

7% off
NZ$6,894
for 7 nights, 1 home
NZ$985 per night
includes taxes & fees
Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.
Stretch out on the leather sectional with daylight coming through windows on two sides.
The fireplace gives everyone a natural place to gather.
Cook, serve, and sit down together across an open space centered on the dining table.
See the cabin's wood exterior and raised deck against a green, wooded slope.
Exceptional
(21 reviews)

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Killington

7% off
NZ$5,286
for 7 nights, 1 cabin
NZ$755 per night
includes taxes & fees
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Kitchen
Kitchen
Living room
Hot Tub
Exceptional
(17 reviews)

Base Camp Retreat at Killington - Trails, Hot Tub, Fire Pit & Game Room

Killington

8% off
NZ$12,824
for 7 nights, 1 home
NZ$1,832 per night
includes taxes & fees
Base Camp Retreat at Killington - Trails, Hot Tub, Fire Pit & Game Room
Two separate beds give travel companions their own place to sleep.
Use the round table by the pass-through for coffee or a casual breakfast close to the kitchen counters.
Spend time together while daylight fills the main seating area.
Good weather is an invitation to move the meal outside.
Exceptional
(6 reviews)

Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort

Rutland

7% off
NZ$5,046
for 7 nights, 1 home
NZ$721 per night
includes taxes & fees
Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort
Across the pond, the chalet's rear deck and tall window wall face a broad lawn edged by trees.
Prep space on the island faces the dining table and tall window wall.
Wash up at the kitchen sink while tall windows frame the pond, lawn, and distant mountains.
A wide sectional wraps the sitting area, while the pool table and hanging chair sit by the windows.
Exceptional
(5 reviews)

Chalet 91 at Killington - 4BR Luxury Lodge with Hot Tub, Sauna, Pool Table

Killington

8% off
NZ$14,902
for 7 nights, 1 home
NZ$2,129 per night
includes taxes & fees
Chalet 91 at Killington - 4BR Luxury Lodge with Hot Tub, Sauna, Pool Table
Dining
Outdoor dining
Exterior
Private kitchen
Exceptional
(125 reviews)

Waterfront Ponds, Beautiful , 51 Acre Property Retreat

Brandon

7% off
NZ$3,386
for 7 nights, 1 home
NZ$484 per night
includes taxes & fees
Waterfront Ponds, Beautiful , 51 Acre Property Retreat
Living area
Outdoor dining
Living area
Living area
Exceptional
(7 reviews)

VT Lodge Cabin w Mountain Views near Killington

Proctor

8% off
NZ$6,106
for 7 nights, 1 cabin
NZ$872 per night
includes taxes & fees
VT Lodge Cabin w Mountain Views near Killington
Living area
Living area
Exterior
Interior
Exceptional
(6 reviews)

Breathtaking Views & Walking Distance to the Fabulous Mountain Top Inn Resort

Chittenden

8% off
NZ$10,062
for 7 nights, 1 home
NZ$1,437 per night
includes taxes & fees
Breathtaking Views & Walking Distance to the Fabulous Mountain Top Inn Resort
Living area
Exterior
Interior
Exterior
Exceptional
(24 reviews)

Unique family-friendly Vermont cabin!

Fair Haven

16% off
NZ$2,504
for 7 nights, 1 cabin
NZ$358 per night
includes taxes & fees
Unique family-friendly Vermont cabin!
Living room and Dining room from the stairs landing
Living area
Living room with cathedral ceiling, wood-burning fireplace, and 50" TV
Mud-room, with firewood and kindling provided
Exceptional
(14 reviews)

Spacious Townhouse on the Killington Access Road

Killington

10% off
NZ$9,240
for 7 nights, 1 home
NZ$1,320 per night
includes taxes & fees
Spacious Townhouse on the Killington Access Road
Property grounds
Living area
Outdoor dining
Looking into second bedroom from Master bedroom.
Exceptional
(49 reviews)

Killington: Cozy Private Home, Central Location

Killington

11% off
NZ$4,730
for 7 nights, 1 home
NZ$676 per night
includes taxes & fees
Killington: Cozy Private Home, Central Location
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Pittsford getaway

Enjoy the museums and other features of Pittsford. Renowned for its skiing, shopping and restaurants, this city welcomes all visitors. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Pittsford

Are you hoping to discover attractions to see during your stay? Venture out of your cosy holiday rental and experience everything that Pittsford has to offer. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Green Mountain National Golf Course (10.1 mi / 16.2 km)
  • Pico Mountain at Killington Ski Resort (10.2 mi / 16.4 km)
  • Pond Hill Ranch and Pro Rodeo (11.1 mi / 17.8 km)
  • Killington Resort (12.8 mi / 20.7 km)
  • Killington Adventure Center (12.8 mi / 20.7 km)
  • Killington Golf Course (12.9 mi / 20.8 km)

Exploring the natural landscape of Pittsford

Whether you're looking for fun outdoor activities or just want to take in the scenery, Pittsford is a great place to get out in nature. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Lake Hortonia (9.3 mi / 15 km)
  • Lake Bomoseen (10.3 mi / 16.6 km)
  • Pico Peak (10.7 mi / 17.2 km)
  • Sunset Lake (12.6 mi / 20.2 km)
  • Killington Peak (12.6 mi / 20.2 km)
  • Lake Dunmore (13.7 mi / 22.1 km)

Travelling to and around Pittsford

Fly into Rutland, VT (RUT-Rutland Southern Vermont Regional), the closest airport, located 13 mi (21 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Springfield, VT (VSF-Hartness State), which is 35.7 mi (57.4 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Pittsford?
The most popular types of holiday homes in Pittsford are houses. Searching for something different? Bookabach has a variety of options to match the unique needs of our guests, so you'll see holiday properties in all sizes and shapes. The ideal fit is ready and waiting for you — discover yours today.
How much does it cost to rent a holiday home in Pittsford?
A number of things affect what you'll pay for your holiday home in Pittsford, including the type of property, length of stay and season. Still, all our holiday homes have something in common — excellent value. Just enter your travel dates to find your perfect match.
How much does it cost to rent a beach house in Pittsford?
Prices for beach houses in Pittsford differ depending on the type and size of the property and when you're travelling. All you need to do is enter your travel dates into Bookabach and how many guests to view your home options and prices. From there you can use the filters to refine your search by ratings, nearby activities, amenities and more.
Are there pet-friendly holiday homes in Pittsford?
Good news! Yes. You'll have your pick of nine holiday homes that allow pets in Pittsford. Many of our pet-friendly holiday homes have a garden for your fur baby to play around in, complimentary treats, special dog beds and proximity to parks and green space. Apply the "Pets allowed" filter to find a holiday home on Bookabach that's pawfect.
Can I rent a house with a pool in Pittsford?
Add a whole other level of fun to your holiday by booking your crew into one of the two houses with a private pool in Pittsford. Use our handy search filter to find the kind of property you want on Bookabach, and then spend carefree days playing and splashing in a swimming pool that's just for you.
What are popular home amenities in Pittsford?
Some of the most popular home amenities people are searching for in Pittsford include nearby museums, a firepit and a barbecue grill. Whether you're on the road with family, buddies or even pets, Bookabach holiday properties include the best amenities for ultimate relaxation with the people you love.
Are there large group holiday homes in Pittsford?
With three holiday homes that can sleep 10 or more people in Pittsford, there's no need to cross anyone off the invite list. From extended family holidays to events like Thanksgiving or Christmas parties, Bookabach will help you find a large group home to match the occasion.
Are there holiday homes in Pittsford that welcome kids?
Bring the entire family together for the adventure of a lifetime in Pittsford at one of our nine family-friendly properties. Lots of these stays offer conveniences that are suitable for trips with youngsters, such as full kitchens, bunk beds and patios. Just click on the "Properties good for families" filter and pick out your favourite.
What are the top attractions for families in Pittsford?
Keep your kids busy at these fun family-friendly attractions in Pittsford:
  • Brandon Museum
  • Green Mountain Rock Climbing Centre
  • Hathaway Farm
Can I find two-bedroom holiday homes in Pittsford?
Pittsford has two two-bedroom holiday properties to select from. Book a holiday home with all the privacy and comfort you're looking for at a fantastic price on Bookabach.
Are there holiday homes with WiFi in Pittsford?
Pittsford has five holiday homes with WiFi, so you'll be able to stay connected while you're travelling. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movie blockbusters to sending emails, these Bookabach homes make it a cinch to go online.
How can I find holiday homes with air conditioning in Pittsford?
You'll have a choice of six Bookabach holiday homes with air conditioning in Pittsford giving you that gentle, cool breeze and extra level of comfort. Enter your preferred travel dates and then use our handy filters to locate stays with air conditioning.
How old do you have to be to rent a holiday home in Pittsford?
The minimum age is typically 16, 18 or 21. It can change across properties on Bookabach, so check the rules of your preferred Pittsford holiday home before booking your escape.
How long can I rent a holiday home in Pittsford for?
It's really down to the Pittsford property. To browse available options offering extended stays, just enter your dates and guest number into Bookabach's search page. You can enjoy having the whole place to yourself, along with the comforts of home like a fully-equipped kitchen and outdoor spaces where the kids can play. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.