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Pittsford Vacation Rentals

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50 rentals in Pittsford.
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Beautiful colonial with 3 fireplace, gourmet kitchen, pool and brand new hot tub, vacation rental in Pittsford
Beautiful colonial with 3 fireplace, gourmet kitchen, pool and brand new hot tub, vacation rental in Pittsford
Beautiful colonial with 3 fireplace, gourmet kitchen, pool and brand new hot tub, vacation rental in Pittsford

Beautiful colonial with 3 fireplace, gourmet kitchen, pool and brand new hot tub

Rental Home
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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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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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
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Idyllic Pittsford Farmhouse~20Mi to Killington Ski, vacation rental in Pittsford
Idyllic Pittsford Farmhouse~20Mi to Killington Ski, vacation rental in Pittsford
Idyllic Pittsford Farmhouse~20Mi to Killington Ski, vacation rental in Pittsford

Idyllic Pittsford Farmhouse~20Mi to Killington Ski

Rental Home
6 bedrooms
3 bathrooms
Sleeps 12
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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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
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Beautiful house minutes from Lake Bomoseen - Dogs Welcome, vacation rental in Pittsford
Beautiful house minutes from Lake Bomoseen - Dogs Welcome, vacation rental in Pittsford
Beautiful house minutes from Lake Bomoseen - Dogs Welcome, vacation rental in Pittsford

Beautiful house minutes from Lake Bomoseen - Dogs Welcome

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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'Ridge Chalet', A-Frame Five BR Home, vacation rental in Pittsford
'Ridge Chalet', A-Frame Five BR Home, vacation rental in Pittsford
'Ridge Chalet', A-Frame Five BR Home, vacation rental in Pittsford

'Ridge Chalet', A-Frame Five BR Home

Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming cottage located on peaceful Lake Bomoseen, vacation rental in Pittsford
Charming cottage located on peaceful Lake Bomoseen, vacation rental in Pittsford
Charming cottage located on peaceful Lake Bomoseen, vacation rental in Pittsford

Charming cottage located on peaceful Lake Bomoseen

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private, Recently Furnished 5 BR Killington All-Season Home With Pool & Hot Tub, vacation rental in Pittsford
Private, Recently Furnished 5 BR Killington All-Season Home With Pool & Hot Tub, vacation rental in Pittsford
Private, Recently Furnished 5 BR Killington All-Season Home With Pool & Hot Tub, vacation rental in Pittsford

Private, Recently Furnished 5 BR Killington All-Season Home With Pool & Hot Tub

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Gigi and Pops’  Secret Cabin. Brand New, vacation rental in Pittsford
Gigi and Pops’  Secret Cabin. Brand New, vacation rental in Pittsford
Gigi and Pops’  Secret Cabin. Brand New, vacation rental in Pittsford

Gigi and Pops’ Secret Cabin. Brand New

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Pico Mountain Resort Ski Chalet, Ski-on/Ski-Off, 4BR/2BA, vacation rental in Pittsford
Pico Mountain Resort Ski Chalet, Ski-on/Ski-Off, 4BR/2BA, vacation rental in Pittsford
Pico Mountain Resort Ski Chalet, Ski-on/Ski-Off, 4BR/2BA, vacation rental in Pittsford

Pico Mountain Resort Ski Chalet, Ski-on/Ski-Off, 4BR/2BA

Rental Home
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Cozy, warm 4 season Lake House, vacation rental in Pittsford
Cozy, warm 4 season Lake House, vacation rental in Pittsford
Cozy, warm 4 season Lake House, vacation rental in Pittsford

Cozy, warm 4 season Lake House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Brand new 2020 Reno of Federal Style House, steps from Downtown Brandon, vacation rental in Pittsford
Brand new 2020 Reno of Federal Style House, steps from Downtown Brandon, vacation rental in Pittsford
Brand new 2020 Reno of Federal Style House, steps from Downtown Brandon, vacation rental in Pittsford

Brand new 2020 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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Killington Condo with 3 Flat Screen TVs, pool & tennis !, vacation rental in Pittsford
Killington Condo with 3 Flat Screen TVs, pool & tennis !, vacation rental in Pittsford
Killington Condo with 3 Flat Screen TVs, pool & tennis !, vacation rental in Pittsford

Killington Condo with 3 Flat Screen TVs, pool & tennis !

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Updated home 3 MIN TO PICO skiing. 15 MIN TO Killington Mtn. LOCATION!!, vacation rental in Pittsford
Updated home 3 MIN TO PICO skiing. 15 MIN TO Killington Mtn. LOCATION!!, vacation rental in Pittsford
Updated home 3 MIN TO PICO skiing. 15 MIN TO Killington Mtn. LOCATION!!, vacation rental in Pittsford

Updated home 3 MIN TO PICO skiing. 15 MIN TO Killington Mtn. LOCATION!!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Family-friendly mountain home w/private hot tub & Ping-Pong - Close to skiing, vacation rental in Pittsford
Family-friendly mountain home w/private hot tub & Ping-Pong - Close to skiing, vacation rental in Pittsford
Family-friendly mountain home w/private hot tub & Ping-Pong - Close to skiing, vacation rental in Pittsford

Family-friendly mountain home w/private hot tub & Ping-Pong - Close to skiing

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Restful and Relaxing Lakeside Cottage on Lake Bomoseen, vacation rental in Pittsford
Restful and Relaxing Lakeside Cottage on Lake Bomoseen, vacation rental in Pittsford
Restful and Relaxing Lakeside Cottage on Lake Bomoseen, vacation rental in Pittsford

Restful and Relaxing Lakeside Cottage on Lake Bomoseen

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Killington Gateway Condominium Unit 12B, vacation rental in Pittsford
Killington Gateway Condominium Unit 12B, vacation rental in Pittsford
Killington Gateway Condominium Unit 12B, vacation rental in Pittsford

Killington Gateway Condominium Unit 12B

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Your Best Home away from Home for your vacation, vacation rental in Pittsford
Your Best Home away from Home for your vacation, vacation rental in Pittsford
Your Best Home away from Home for your vacation, vacation rental in Pittsford

Your Best Home away from Home for your vacation

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Secluded Killington Mountain Getaway; 2 min to Pico and 5 min to Killington, vacation rental in Pittsford
Secluded Killington Mountain Getaway; 2 min to Pico and 5 min to Killington, vacation rental in Pittsford
Secluded Killington Mountain Getaway; 2 min to Pico and 5 min to Killington, vacation rental in Pittsford

Secluded Killington Mountain Getaway; 2 min to Pico and 5 min to Killington

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Dog-friendly cottage w/ deck & beautiful views - close to golf, skiing, & trail, vacation rental in Pittsford
Dog-friendly cottage w/ deck & beautiful views - close to golf, skiing, & trail, vacation rental in Pittsford
Dog-friendly cottage w/ deck & beautiful views - close to golf, skiing, & trail, vacation rental in Pittsford

Dog-friendly cottage w/ deck & beautiful views - close to golf, skiing, & trail

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Ski in/out Condo on Pico Mountain at Killington Ski Resort, vacation rental in Pittsford
Ski in/out Condo on Pico Mountain at Killington Ski Resort, vacation rental in Pittsford
Ski in/out Condo on Pico Mountain at Killington Ski Resort, vacation rental in Pittsford

Ski in/out Condo on Pico Mountain at Killington Ski Resort

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
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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Killington- 6 Bedroom, 3 Bath in the Heart of Killington!, vacation rental in Pittsford
Killington- 6 Bedroom, 3 Bath in the Heart of Killington!, vacation rental in Pittsford
Killington- 6 Bedroom, 3 Bath in the Heart of Killington!, vacation rental in Pittsford

Killington- 6 Bedroom, 3 Bath in the Heart of Killington!

Rental Home
6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
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Killington Getaway In Private Community, vacation rental in Pittsford
Killington Getaway In Private Community, vacation rental in Pittsford
Killington Getaway In Private Community, vacation rental in Pittsford

Killington Getaway In Private Community

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Killington Rental *Seasonal, Yearly, Weekday and Weekends Available for Discount, vacation rental in Pittsford
Killington Rental *Seasonal, Yearly, Weekday and Weekends Available for Discount, vacation rental in Pittsford
Killington Rental *Seasonal, Yearly, Weekday and Weekends Available for Discount, vacation rental in Pittsford

Killington Rental *Seasonal, Yearly, Weekday and Weekends Available for Discount

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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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Spacious Rutland Townhome w/Fire Pit- Walk to Town, vacation rental in Pittsford
Spacious Rutland Townhome w/Fire Pit- Walk to Town, vacation rental in Pittsford
Spacious Rutland Townhome w/Fire Pit- Walk to Town, vacation rental in Pittsford

Spacious Rutland Townhome w/Fire Pit- Walk to Town

Rental Home
4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
More info
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Your Best Home away from Home for your vacation, vacation rental in Pittsford
Your Best Home away from Home for your vacation, vacation rental in Pittsford
Your Best Home away from Home for your vacation, vacation rental in Pittsford

Your Best Home away from Home for your vacation

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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State of the art, newly renovated mountain home., vacation rental in Pittsford
State of the art, newly renovated mountain home., vacation rental in Pittsford
State of the art, newly renovated mountain home., vacation rental in Pittsford

State of the art, newly renovated mountain home.

Rental Home
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Lovely apartment w/in walking distance to slopes - year-round outdoor activities, vacation rental in Pittsford
Lovely apartment w/in walking distance to slopes - year-round outdoor activities, vacation rental in Pittsford
Lovely apartment w/in walking distance to slopes - year-round outdoor activities, vacation rental in Pittsford

Lovely apartment w/in walking distance to slopes - year-round outdoor activities

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Far Enough, An Old World Vermont Estate, vacation rental in Pittsford
Far Enough, An Old World Vermont Estate, vacation rental in Pittsford
Far Enough, An Old World Vermont Estate, vacation rental in Pittsford

Far Enough, An Old World Vermont Estate

Rental Home
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
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Killington- 4 Bedroom, 2 Bath, Onsite Laundry, vacation rental in Pittsford
Killington- 4 Bedroom, 2 Bath, Onsite Laundry, vacation rental in Pittsford
Killington- 4 Bedroom, 2 Bath, Onsite Laundry, vacation rental in Pittsford

Killington- 4 Bedroom, 2 Bath, Onsite Laundry

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Cabin 1 Killington / Rutland Clean, Comfortable 1 Bedroom Cabin, vacation rental in Pittsford
Cabin 1 Killington / Rutland Clean, Comfortable 1 Bedroom Cabin, vacation rental in Pittsford
Cabin 1 Killington / Rutland Clean, Comfortable 1 Bedroom Cabin, vacation rental in Pittsford

Cabin 1 Killington / Rutland Clean, Comfortable 1 Bedroom Cabin

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Cabin 4 Killington / Rutland Clean, Comfortable 2 Bedroom Cabin, vacation rental in Pittsford
Cabin 4 Killington / Rutland Clean, Comfortable 2 Bedroom Cabin, vacation rental in Pittsford
Cabin 4 Killington / Rutland Clean, Comfortable 2 Bedroom Cabin, vacation rental in Pittsford

Cabin 4 Killington / Rutland Clean, Comfortable 2 Bedroom Cabin

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Spectacular Water Views From Every Room ~ Directly On Lake Hortonia, Vt., vacation rental in Pittsford
Spectacular Water Views From Every Room ~ Directly On Lake Hortonia, Vt., vacation rental in Pittsford
Spectacular Water Views From Every Room ~ Directly On Lake Hortonia, Vt., vacation rental in Pittsford

Spectacular Water Views From Every Room ~ Directly On Lake Hortonia, Vt.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Killington- 6 Bedroom, 3 Bath. Right in the heart of Ski country!, vacation rental in Pittsford
Killington- 6 Bedroom, 3 Bath. Right in the heart of Ski country!, vacation rental in Pittsford
Killington- 6 Bedroom, 3 Bath. Right in the heart of Ski country!, vacation rental in Pittsford

Killington- 6 Bedroom, 3 Bath. Right in the heart of Ski country!

Rental Home
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Killington Vermont- 2 Bedroom/1Bath. Right in the heart of Ski country!, vacation rental in Pittsford
Killington Vermont- 2 Bedroom/1Bath. Right in the heart of Ski country!, vacation rental in Pittsford
Killington Vermont- 2 Bedroom/1Bath. Right in the heart of Ski country!, vacation rental in Pittsford

Killington Vermont- 2 Bedroom/1Bath. Right in the heart of Ski country!

Rental Home
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Killington Vermont - 4 Bedroom, 2 Bath. Right in the heart of ski country!, vacation rental in Pittsford
Killington Vermont - 4 Bedroom, 2 Bath. Right in the heart of ski country!, vacation rental in Pittsford
Killington Vermont - 4 Bedroom, 2 Bath. Right in the heart of ski country!, vacation rental in Pittsford

Killington Vermont - 4 Bedroom, 2 Bath. Right in the heart of ski country!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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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Journey's End Manor - Historical, vacation rental in Pittsford
Journey's End Manor - Historical, vacation rental in Pittsford
Journey's End Manor - Historical, vacation rental in Pittsford

Journey's End Manor - Historical

Rental Home
7 bedrooms
5 bathrooms
Sleeps 17
Match: Sleeps
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Brand New 1200 Sq ft Apartment Fully Furnished - brand NEW!, vacation rental in Pittsford
Brand New 1200 Sq ft Apartment Fully Furnished - brand NEW!, vacation rental in Pittsford
Brand New 1200 Sq ft Apartment Fully Furnished - brand NEW!, vacation rental in Pittsford

Brand New 1200 Sq ft Apartment Fully Furnished - brand NEW!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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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
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Cortina Mountain Chalet - Outdoor Hot Tub - Minutes to Pico Mountain, vacation rental in Pittsford
Cortina Mountain Chalet - Outdoor Hot Tub - Minutes to Pico Mountain, vacation rental in Pittsford
Cortina Mountain Chalet - Outdoor Hot Tub - Minutes to Pico Mountain, vacation rental in Pittsford

Cortina Mountain Chalet - Outdoor Hot Tub - Minutes to Pico Mountain

Rental Home
3 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
More info
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Left Duplex Home Directly Across From Pico Mountain, Close to Killington. Free c, vacation rental in Pittsford
Left Duplex Home Directly Across From Pico Mountain, Close to Killington. Free c, vacation rental in Pittsford
Left Duplex Home Directly Across From Pico Mountain, Close to Killington. Free c, vacation rental in Pittsford

Left Duplex Home Directly Across From Pico Mountain, Close to Killington. Free c

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Cabin 2 Killington / Rutland Clean Comfortable 2 Bedroom Cabin , vacation rental in Pittsford
Cabin 2 Killington / Rutland Clean Comfortable 2 Bedroom Cabin , vacation rental in Pittsford
Cabin 2 Killington / Rutland Clean Comfortable 2 Bedroom Cabin , vacation rental in Pittsford

Cabin 2 Killington / Rutland Clean Comfortable 2 Bedroom Cabin

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Cortina Mountain Chalet, vacation rental in Pittsford
Cortina Mountain Chalet, vacation rental in Pittsford
Cortina Mountain Chalet, vacation rental in Pittsford

Cortina Mountain Chalet

Rental Home
3 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
More info
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Killington market, making it ideal for vacation or rental use, vacation rental in Pittsford
Killington market, making it ideal for vacation or rental use, vacation rental in Pittsford
Killington market, making it ideal for vacation or rental use, vacation rental in Pittsford

Killington market, making it ideal for vacation or rental use

Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Massive Ski Chalet equipped with Custom WFH Space, vacation rental in Pittsford
Massive Ski Chalet equipped with Custom WFH Space, vacation rental in Pittsford
Massive Ski Chalet equipped with Custom WFH Space, vacation rental in Pittsford

Massive Ski Chalet equipped with Custom WFH Space

Rental Home
7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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