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Pittsford Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
50 rentals in Pittsford.
Farmhouse with gracious grounds/Killington sking/campus weekends, Middlebury,, vacation rental in Pittsford
Farmhouse with gracious grounds/Killington sking/campus weekends, Middlebury,, vacation rental in Pittsford
Farmhouse with gracious grounds/Killington sking/campus weekends, Middlebury,, vacation rental in Pittsford

Farmhouse with gracious grounds/Killington sking/campus weekends, Middlebury,

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Norm’s Place, vacation rental in Pittsford
Norm’s Place, vacation rental in Pittsford
Norm’s Place, vacation rental in Pittsford

Norm’s Place

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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1806 Carriage House with antiques, fireplace, luxury sheets and down comforters., vacation rental in Pittsford
1806 Carriage House with antiques, fireplace, luxury sheets and down comforters., vacation rental in Pittsford
1806 Carriage House with antiques, fireplace, luxury sheets and down comforters., vacation rental in Pittsford

1806 Carriage House with antiques, fireplace, luxury sheets and down comforters.

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Pastoral home with gas fireplace & lovely view - great for skiing & fall foliage, vacation rental in Pittsford
Pastoral home with gas fireplace & lovely view - great for skiing & fall foliage, vacation rental in Pittsford
Pastoral home with gas fireplace & lovely view - great for skiing & fall foliage, vacation rental in Pittsford

Pastoral home with gas fireplace & lovely view - great for skiing & fall foliage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Newly renovated 3 bedroom home near 4 ski areas, vacation rental in Pittsford
Newly renovated 3 bedroom home near 4 ski areas, vacation rental in Pittsford
Newly renovated 3 bedroom home near 4 ski areas, vacation rental in Pittsford

Newly renovated 3 bedroom home near 4 ski areas

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Seasonal Rental!  2,700SF home w/hot tub 20 minutes to Killington, vacation rental in Pittsford
Seasonal Rental!  2,700SF home w/hot tub 20 minutes to Killington, vacation rental in Pittsford
Seasonal Rental!  2,700SF home w/hot tub 20 minutes to Killington, vacation rental in Pittsford

Seasonal Rental! 2,700SF home w/hot tub 20 minutes to Killington

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The following properties within 20 miles of Pittsford match all your filters:
Pond View Cabin, vacation rental in Pittsford
Pond View Cabin, vacation rental in Pittsford
Pond View Cabin, vacation rental in Pittsford

Pond View Cabin

Cabin
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill, vacation rental in Pittsford
6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill, vacation rental in Pittsford
6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill, vacation rental in Pittsford

6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Breathtaking Views & Walking Distance to the Fabulous Mountain Top Inn Resort, vacation rental in Pittsford
Breathtaking Views & Walking Distance to the Fabulous Mountain Top Inn Resort, vacation rental in Pittsford
Breathtaking Views & Walking Distance to the Fabulous Mountain Top Inn Resort, vacation rental in Pittsford

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon, vacation rental in Pittsford
Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon, vacation rental in Pittsford
Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon, vacation rental in Pittsford

Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Waterfront Ponds,  Beautiful  , 51 Acre Property Retreat, vacation rental in Pittsford
Waterfront Ponds,  Beautiful  , 51 Acre Property Retreat, vacation rental in Pittsford
Waterfront Ponds,  Beautiful  , 51 Acre Property Retreat, vacation rental in Pittsford

Waterfront Ponds, Beautiful , 51 Acre Property Retreat

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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Secluded Ski Condo near Killington w/ Fast WiFi, Shared Outdoor Pool & Tennis, vacation rental in Pittsford
Secluded Ski Condo near Killington w/ Fast WiFi, Shared Outdoor Pool & Tennis, vacation rental in Pittsford
Secluded Ski Condo near Killington w/ Fast WiFi, Shared Outdoor Pool & Tennis, vacation rental in Pittsford

Secluded Ski Condo near Killington w/ Fast WiFi, Shared Outdoor Pool & Tennis

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Cozy Home, Minutes from Killington! Washer/Dryer & Free Disney+/Peacock!, vacation rental in Pittsford
Cozy Home, Minutes from Killington! Washer/Dryer & Free Disney+/Peacock!, vacation rental in Pittsford
Cozy Home, Minutes from Killington! Washer/Dryer & Free Disney+/Peacock!, vacation rental in Pittsford

Cozy Home, Minutes from Killington! Washer/Dryer & Free Disney+/Peacock!

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Next To Mountain Top Inn - Close to Killington, Spectacular Mountain/Lake Views., vacation rental in Pittsford
Next To Mountain Top Inn - Close to Killington, Spectacular Mountain/Lake Views., vacation rental in Pittsford
Next To Mountain Top Inn - Close to Killington, Spectacular Mountain/Lake Views., vacation rental in Pittsford

Next To Mountain Top Inn - Close to Killington, Spectacular Mountain/Lake Views.

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Ski condo close to multiple resorts, vacation rental in Pittsford
Ski condo close to multiple resorts, vacation rental in Pittsford
Ski condo close to multiple resorts, vacation rental in Pittsford

Ski condo close to multiple resorts

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Cozy home 13 minutes from Killington- child & dog friendly, vacation rental in Pittsford
Cozy home 13 minutes from Killington- child & dog friendly, vacation rental in Pittsford
Cozy home 13 minutes from Killington- child & dog friendly, vacation rental in Pittsford

Cozy home 13 minutes from Killington- child & dog friendly

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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The Proctor Escape, vacation rental in Pittsford
The Proctor Escape, vacation rental in Pittsford
The Proctor Escape, vacation rental in Pittsford

The Proctor Escape

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Red Clover Inn-Accessible King Suite in Killington, vacation rental in Pittsford
Red Clover Inn-Accessible King Suite in Killington, vacation rental in Pittsford
Red Clover Inn-Accessible King Suite in Killington, vacation rental in Pittsford

Red Clover Inn-Accessible King Suite in Killington

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Red Clover Inn Romantic King Suite near Killington, vacation rental in Pittsford
Red Clover Inn Romantic King Suite near Killington, vacation rental in Pittsford
Red Clover Inn Romantic King Suite near Killington, vacation rental in Pittsford

Red Clover Inn Romantic King Suite near Killington

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Red Clover Inn 2-story Queen Suite near Killington, vacation rental in Pittsford
Red Clover Inn 2-story Queen Suite near Killington, vacation rental in Pittsford
Red Clover Inn 2-story Queen Suite near Killington, vacation rental in Pittsford

Red Clover Inn 2-story Queen Suite near Killington

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Red Clover Inn Spacious King Suite near Killington, vacation rental in Pittsford
Red Clover Inn Spacious King Suite near Killington, vacation rental in Pittsford
Red Clover Inn Spacious King Suite near Killington, vacation rental in Pittsford

Red Clover Inn Spacious King Suite near Killington

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Red Clover Inn: Romantic Queen Suite Killington, vacation rental in Pittsford
Red Clover Inn: Romantic Queen Suite Killington, vacation rental in Pittsford
Red Clover Inn: Romantic Queen Suite Killington, vacation rental in Pittsford

Red Clover Inn: Romantic Queen Suite Killington

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Red Clover Inn: Queen Suite + sofabed Killington, vacation rental in Pittsford
Red Clover Inn: Queen Suite + sofabed Killington, vacation rental in Pittsford
Red Clover Inn: Queen Suite + sofabed Killington, vacation rental in Pittsford

Red Clover Inn: Queen Suite + sofabed Killington

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Red Clover Inn Majestic King Suite near Killington, vacation rental in Pittsford
Red Clover Inn Majestic King Suite near Killington, vacation rental in Pittsford
Red Clover Inn Majestic King Suite near Killington, vacation rental in Pittsford

Red Clover Inn Majestic King Suite near Killington

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Dog-friendly duplex near Pico & Killington with firepit, back porch, streaming, vacation rental in Pittsford
Dog-friendly duplex near Pico & Killington with firepit, back porch, streaming, vacation rental in Pittsford
Dog-friendly duplex near Pico & Killington with firepit, back porch, streaming, vacation rental in Pittsford

Dog-friendly duplex near Pico & Killington with firepit, back porch, streaming

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Pond View Cabin-Rustic 2 Bedroom-Sleeps 4, vacation rental in Pittsford
Pond View Cabin-Rustic 2 Bedroom-Sleeps 4, vacation rental in Pittsford
Pond View Cabin-Rustic 2 Bedroom-Sleeps 4, vacation rental in Pittsford

Pond View Cabin-Rustic 2 Bedroom-Sleeps 4

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Killington Mountain Ski resort five minutes away, vacation rental in Pittsford
Killington Mountain Ski resort five minutes away, vacation rental in Pittsford
Killington Mountain Ski resort five minutes away, vacation rental in Pittsford

Killington Mountain Ski resort five minutes away

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
More info
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Red Clover Inn Two Bedroom Suite near Killington, vacation rental in Pittsford
Red Clover Inn Two Bedroom Suite near Killington, vacation rental in Pittsford
Red Clover Inn Two Bedroom Suite near Killington, vacation rental in Pittsford

Red Clover Inn Two Bedroom Suite near Killington

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Secluded home with electric grill, patio, on-site pool, tennis & laundry room, vacation rental in Pittsford
Secluded home with electric grill, patio, on-site pool, tennis & laundry room, vacation rental in Pittsford
Secluded home with electric grill, patio, on-site pool, tennis & laundry room, vacation rental in Pittsford

Secluded home with electric grill, patio, on-site pool, tennis & laundry room

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Dog-friendly, private oasis just outside town w/ free WiFi, Fire TV, and deck!, vacation rental in Pittsford
Dog-friendly, private oasis just outside town w/ free WiFi, Fire TV, and deck!, vacation rental in Pittsford
Dog-friendly, private oasis just outside town w/ free WiFi, Fire TV, and deck!, vacation rental in Pittsford

Dog-friendly, private oasis just outside town w/ free WiFi, Fire TV, and deck!

Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Luxurious guest home with private art gallery in the heart of a historic village, vacation rental in Pittsford
Luxurious guest home with private art gallery in the heart of a historic village, vacation rental in Pittsford
Luxurious guest home with private art gallery in the heart of a historic village, vacation rental in Pittsford

Luxurious guest home with private art gallery in the heart of a historic village

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Rutland VT mid-town home, vacation rental in Pittsford
Rutland VT mid-town home, vacation rental in Pittsford
Rutland VT mid-town home, vacation rental in Pittsford

Rutland VT mid-town home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Killington Area Private Home, 3 Bd, 2 BR, Sleeps 11+, vacation rental in Pittsford
Killington Area Private Home, 3 Bd, 2 BR, Sleeps 11+, vacation rental in Pittsford
Killington Area Private Home, 3 Bd, 2 BR, Sleeps 11+, vacation rental in Pittsford

Killington Area Private Home, 3 Bd, 2 BR, Sleeps 11+

Rental Home
3 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
More info
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*Restored, Riverside Home*Walk to AdorableDowntown, vacation rental in Pittsford
*Restored, Riverside Home*Walk to AdorableDowntown, vacation rental in Pittsford
*Restored, Riverside Home*Walk to AdorableDowntown, vacation rental in Pittsford

*Restored, Riverside Home*Walk to AdorableDowntown

Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Cozy 3 Bedroom home near Killington, vacation rental in Pittsford
Cozy 3 Bedroom home near Killington, vacation rental in Pittsford
Cozy 3 Bedroom home near Killington, vacation rental in Pittsford

Cozy 3 Bedroom home near Killington

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Private and Peaceful Home Close to Mountain Top Inn and Killington-Pico Resorts, vacation rental in Pittsford
Private and Peaceful Home Close to Mountain Top Inn and Killington-Pico Resorts, vacation rental in Pittsford
Private and Peaceful Home Close to Mountain Top Inn and Killington-Pico Resorts, vacation rental in Pittsford

Private and Peaceful Home Close to Mountain Top Inn and Killington-Pico Resorts

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Chic Brandon Cabin w/ Pool, Hot Tub + Sauna!, vacation rental in Pittsford
Chic Brandon Cabin w/ Pool, Hot Tub + Sauna!, vacation rental in Pittsford
Chic Brandon Cabin w/ Pool, Hot Tub + Sauna!, vacation rental in Pittsford

Chic Brandon Cabin w/ Pool, Hot Tub + Sauna!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Centrally located home near outdoor activities & town with private W/D, vacation rental in Pittsford
Centrally located home near outdoor activities & town with private W/D, vacation rental in Pittsford
Centrally located home near outdoor activities & town with private W/D, vacation rental in Pittsford

Centrally located home near outdoor activities & town with private W/D

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Winter Lore, vacation rental in Pittsford
Winter Lore, vacation rental in Pittsford
Winter Lore, vacation rental in Pittsford

Winter Lore

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Updated Home in Heart of Rutland, Near Slopes, vacation rental in Pittsford
Updated Home in Heart of Rutland, Near Slopes, vacation rental in Pittsford
Updated Home in Heart of Rutland, Near Slopes, vacation rental in Pittsford

Updated Home in Heart of Rutland, Near Slopes

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Winter Lore - Outdoor Hot Tub - Pet Friendly, vacation rental in Pittsford
Winter Lore - Outdoor Hot Tub - Pet Friendly, vacation rental in Pittsford
Winter Lore - Outdoor Hot Tub - Pet Friendly, vacation rental in Pittsford

Winter Lore - Outdoor Hot Tub - Pet Friendly

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Killington VT Escape, vacation rental in Pittsford
Killington VT Escape, vacation rental in Pittsford
Killington VT Escape, vacation rental in Pittsford

Killington VT Escape

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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2400sq.ft of relaxation. Only 7-10 Miles from Killington and Pico, vacation rental in Pittsford
2400sq.ft of relaxation. Only 7-10 Miles from Killington and Pico, vacation rental in Pittsford
2400sq.ft of relaxation. Only 7-10 Miles from Killington and Pico, vacation rental in Pittsford

2400sq.ft of relaxation. Only 7-10 Miles from Killington and Pico

Rental Home
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
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Private Chalet with Custom WFH Space and Hot Tub, vacation rental in Pittsford
Private Chalet with Custom WFH Space and Hot Tub, vacation rental in Pittsford
Private Chalet with Custom WFH Space and Hot Tub, vacation rental in Pittsford

Private Chalet with Custom WFH Space and Hot Tub

Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
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Contemporary Spacious 7br/6.5 bath home near Killington VT, vacation rental in Pittsford
Contemporary Spacious 7br/6.5 bath home near Killington VT, vacation rental in Pittsford
Contemporary Spacious 7br/6.5 bath home near Killington VT, vacation rental in Pittsford

Contemporary Spacious 7br/6.5 bath home near Killington VT

Rental Home
7 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps
More info
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Luxury 7BR/6.5BA Mountain Retreat with Sauna, Hot Tub, and Stunning Views, vacation rental in Pittsford
Luxury 7BR/6.5BA Mountain Retreat with Sauna, Hot Tub, and Stunning Views, vacation rental in Pittsford
Luxury 7BR/6.5BA Mountain Retreat with Sauna, Hot Tub, and Stunning Views, vacation rental in Pittsford

Luxury 7BR/6.5BA Mountain Retreat with Sauna, Hot Tub, and Stunning Views

Rental Home
7 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps
More info
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Red Clover Inn 7-bedroom House (sleeps max 19), vacation rental in Pittsford
Red Clover Inn 7-bedroom House (sleeps max 19), vacation rental in Pittsford
Red Clover Inn 7-bedroom House (sleeps max 19), vacation rental in Pittsford

Red Clover Inn 7-bedroom House (sleeps max 19)

Rental Home
7 bedrooms
10 bathrooms
Sleeps 18
Match: Sleeps
More info
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Blue Ridge Chalet, vacation rental in Pittsford
Blue Ridge Chalet, vacation rental in Pittsford
Blue Ridge Chalet, vacation rental in Pittsford

Blue Ridge Chalet

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Gateway Condominium Unit 25, vacation rental in Pittsford
Gateway Condominium Unit 25, vacation rental in Pittsford
Gateway Condominium Unit 25, vacation rental in Pittsford

Gateway Condominium Unit 25

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views, Grill, vacation rental in Pittsford
6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views, Grill, vacation rental in Pittsford
6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views, Grill, vacation rental in Pittsford

6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views, Grill

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Frequently Asked Questions about Pittsford