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Middlesex Vacation Rentals

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50 rentals in Middlesex.
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Sunnyside Shore - Lakefront Retreat, 2 bedroom, 1 bathroom, sleeps 4-6, vacation rental in Middlesex
Sunnyside Shore - Lakefront Retreat, 2 bedroom, 1 bathroom, sleeps 4-6, vacation rental in Middlesex
Sunnyside Shore - Lakefront Retreat, 2 bedroom, 1 bathroom, sleeps 4-6, vacation rental in Middlesex

Sunnyside Shore - Lakefront Retreat, 2 bedroom, 1 bathroom, sleeps 4-6

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Timber-Frame Cottage - Canandaigua Lake, vacation rental in Middlesex
Beautiful Timber-Frame Cottage - Canandaigua Lake, vacation rental in Middlesex
Beautiful Timber-Frame Cottage - Canandaigua Lake, vacation rental in Middlesex

Beautiful Timber-Frame Cottage - Canandaigua Lake

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Ltd Availability; 2 Steps Access --4BR/3BA--110 Ft Flat Beachfront--Family Home, vacation rental in Middlesex
Ltd Availability; 2 Steps Access --4BR/3BA--110 Ft Flat Beachfront--Family Home, vacation rental in Middlesex
Ltd Availability; 2 Steps Access --4BR/3BA--110 Ft Flat Beachfront--Family Home, vacation rental in Middlesex

Ltd Availability; 2 Steps Access --4BR/3BA--110 Ft Flat Beachfront--Family Home

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Canandaigua Lake Getaway, vacation rental in Middlesex
Canandaigua Lake Getaway, vacation rental in Middlesex
Canandaigua Lake Getaway, vacation rental in Middlesex

Canandaigua Lake Getaway

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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2 bedrooms, 1 Queen size sleeper sofa, 1 Bathroom - Sleeps 6, vacation rental in Middlesex
2 bedrooms, 1 Queen size sleeper sofa, 1 Bathroom - Sleeps 6, vacation rental in Middlesex
2 bedrooms, 1 Queen size sleeper sofa, 1 Bathroom - Sleeps 6, vacation rental in Middlesex

2 bedrooms, 1 Queen size sleeper sofa, 1 Bathroom - Sleeps 6

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Eagle Cove:'Perfect Canandaigua Lake Home for Nature Lovers', vacation rental in Middlesex
Eagle Cove:'Perfect Canandaigua Lake Home for Nature Lovers', vacation rental in Middlesex
Eagle Cove:'Perfect Canandaigua Lake Home for Nature Lovers', vacation rental in Middlesex

Eagle Cove:'Perfect Canandaigua Lake Home for Nature Lovers'

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NEW! 'Aunt Al's Place' w/ Private Deck & Fire Pit!, vacation rental in Middlesex
NEW! 'Aunt Al's Place' w/ Private Deck & Fire Pit!, vacation rental in Middlesex
NEW! 'Aunt Al's Place' w/ Private Deck & Fire Pit!, vacation rental in Middlesex

NEW! 'Aunt Al's Place' w/ Private Deck & Fire Pit!

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Canandaigua Lake's Sunnyside Sunset Retreat, vacation rental in Middlesex
Canandaigua Lake's Sunnyside Sunset Retreat, vacation rental in Middlesex
Canandaigua Lake's Sunnyside Sunset Retreat, vacation rental in Middlesex

Canandaigua Lake's Sunnyside Sunset Retreat

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Quiet elegance on Canandaigua Lake!, vacation rental in Middlesex
Quiet elegance on Canandaigua Lake!, vacation rental in Middlesex
Quiet elegance on Canandaigua Lake!, vacation rental in Middlesex

Quiet elegance on Canandaigua Lake!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Sunset Cove: 'Canandaigua Lake Bliss!', vacation rental in Middlesex
Sunset Cove: 'Canandaigua Lake Bliss!', vacation rental in Middlesex
Sunset Cove: 'Canandaigua Lake Bliss!', vacation rental in Middlesex

Sunset Cove: 'Canandaigua Lake Bliss!'

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Amazing Canandaigua Lake Retreat 4 bed/3 bath/1750 sq ft. Rare End Unit-5 Stars!, vacation rental in Middlesex
Amazing Canandaigua Lake Retreat 4 bed/3 bath/1750 sq ft. Rare End Unit-5 Stars!, vacation rental in Middlesex
Amazing Canandaigua Lake Retreat 4 bed/3 bath/1750 sq ft. Rare End Unit-5 Stars!, vacation rental in Middlesex

Amazing Canandaigua Lake Retreat 4 bed/3 bath/1750 sq ft. Rare End Unit-5 Stars!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Dramatic Views!  Nature's Wonderland. 5 Minutes from Bristol Mountain, vacation rental in Middlesex
Dramatic Views!  Nature's Wonderland. 5 Minutes from Bristol Mountain, vacation rental in Middlesex
Dramatic Views!  Nature's Wonderland. 5 Minutes from Bristol Mountain, vacation rental in Middlesex

Dramatic Views! Nature's Wonderland. 5 Minutes from Bristol Mountain

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Newly renovated romantic lakefront cottage with incredible sunset and lake views, vacation rental in Middlesex
Newly renovated romantic lakefront cottage with incredible sunset and lake views, vacation rental in Middlesex
Newly renovated romantic lakefront cottage with incredible sunset and lake views, vacation rental in Middlesex

Newly renovated romantic lakefront cottage with incredible sunset and lake views

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Heron Cove Sanctuary - Peace, Privacy & Beauty!, vacation rental in Middlesex
Heron Cove Sanctuary - Peace, Privacy & Beauty!, vacation rental in Middlesex
Heron Cove Sanctuary - Peace, Privacy & Beauty!, vacation rental in Middlesex

Heron Cove Sanctuary - Peace, Privacy & Beauty!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Paradise on the Lake, vacation rental in Middlesex
Paradise on the Lake, vacation rental in Middlesex
Paradise on the Lake, vacation rental in Middlesex

Paradise on the Lake

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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3 Bedroom Townhouse in scenic Bristol Harbor Village, vacation rental in Middlesex
3 Bedroom Townhouse in scenic Bristol Harbor Village, vacation rental in Middlesex
3 Bedroom Townhouse in scenic Bristol Harbor Village, vacation rental in Middlesex

3 Bedroom Townhouse in scenic Bristol Harbor Village

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Canandaigua Lake Front Cliffside Condo: Bristol Harbour, Beach & Skiing!, vacation rental in Middlesex
Canandaigua Lake Front Cliffside Condo: Bristol Harbour, Beach & Skiing!, vacation rental in Middlesex
Canandaigua Lake Front Cliffside Condo: Bristol Harbour, Beach & Skiing!, vacation rental in Middlesex

Canandaigua Lake Front Cliffside Condo: Bristol Harbour, Beach & Skiing!

Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Breathtaking Canandaigua Lake Home In A Quiet Cove, vacation rental in Middlesex
Breathtaking Canandaigua Lake Home In A Quiet Cove, vacation rental in Middlesex
Breathtaking Canandaigua Lake Home In A Quiet Cove, vacation rental in Middlesex

Breathtaking Canandaigua Lake Home In A Quiet Cove

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Finger Lakes Wine Country Lake View Ski Loft/Lake Home In Bristol Harbour Resort, vacation rental in Middlesex
Finger Lakes Wine Country Lake View Ski Loft/Lake Home In Bristol Harbour Resort, vacation rental in Middlesex
Finger Lakes Wine Country Lake View Ski Loft/Lake Home In Bristol Harbour Resort, vacation rental in Middlesex

Finger Lakes Wine Country Lake View Ski Loft/Lake Home In Bristol Harbour Resort

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Canandaigua / Bristol Harbour Lakeside Condo -All Season Resort!, vacation rental in Middlesex
Canandaigua / Bristol Harbour Lakeside Condo -All Season Resort!, vacation rental in Middlesex
Canandaigua / Bristol Harbour Lakeside Condo -All Season Resort!, vacation rental in Middlesex

Canandaigua / Bristol Harbour Lakeside Condo -All Season Resort!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Canandaigua Lake,  Seneca Pt, 4BR's en Suite sleeping 8,  BR's all now with AC, vacation rental in Middlesex
Canandaigua Lake,  Seneca Pt, 4BR's en Suite sleeping 8,  BR's all now with AC, vacation rental in Middlesex
Canandaigua Lake,  Seneca Pt, 4BR's en Suite sleeping 8,  BR's all now with AC, vacation rental in Middlesex

Canandaigua Lake, Seneca Pt, 4BR's en Suite sleeping 8, BR's all now with AC

Rental Home
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Deer View: 'Modern Condo Minutes from Bristol Ski Mountain and Wineries', vacation rental in Middlesex
Deer View: 'Modern Condo Minutes from Bristol Ski Mountain and Wineries', vacation rental in Middlesex
Deer View: 'Modern Condo Minutes from Bristol Ski Mountain and Wineries', vacation rental in Middlesex

Deer View: 'Modern Condo Minutes from Bristol Ski Mountain and Wineries'

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Gorgeous Canandaigua Lake Front Condo, vacation rental in Middlesex
Gorgeous Canandaigua Lake Front Condo, vacation rental in Middlesex
Gorgeous Canandaigua Lake Front Condo, vacation rental in Middlesex

Gorgeous Canandaigua Lake Front Condo

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Birches-Peaceful resort retreat in finger lakes wine country, vacation rental in Middlesex
The Birches-Peaceful resort retreat in finger lakes wine country, vacation rental in Middlesex
The Birches-Peaceful resort retreat in finger lakes wine country, vacation rental in Middlesex

The Birches-Peaceful resort retreat in finger lakes wine country

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Spectacular 100 acres on the shores of Lake Canandaigua, vacation rental in Middlesex
Spectacular 100 acres on the shores of Lake Canandaigua, vacation rental in Middlesex
Spectacular 100 acres on the shores of Lake Canandaigua, vacation rental in Middlesex

Spectacular 100 acres on the shores of Lake Canandaigua

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Luxurious Finger Lakes Home w/ Home Gym, Game Room, vacation rental in Middlesex
Luxurious Finger Lakes Home w/ Home Gym, Game Room, vacation rental in Middlesex
Luxurious Finger Lakes Home w/ Home Gym, Game Room, vacation rental in Middlesex

Luxurious Finger Lakes Home w/ Home Gym, Game Room

Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Private getaway cabin in the woods, vacation rental in Middlesex
Private getaway cabin in the woods, vacation rental in Middlesex
Private getaway cabin in the woods, vacation rental in Middlesex

Private getaway cabin in the woods

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Lakefront Retreat, vacation rental in Middlesex
Lakefront Retreat, vacation rental in Middlesex
Lakefront Retreat, vacation rental in Middlesex

Lakefront Retreat

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cliffside Sunrise: 'Gorgeous Canandaigua Lake Views!', vacation rental in Middlesex
Cliffside Sunrise: 'Gorgeous Canandaigua Lake Views!', vacation rental in Middlesex
Cliffside Sunrise: 'Gorgeous Canandaigua Lake Views!', vacation rental in Middlesex

Cliffside Sunrise: 'Gorgeous Canandaigua Lake Views!'

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Arbor Landing:'Amazing Charm & History', vacation rental in Middlesex
Arbor Landing:'Amazing Charm & History', vacation rental in Middlesex
Arbor Landing:'Amazing Charm & History', vacation rental in Middlesex

Arbor Landing:'Amazing Charm & History'

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Bogie's Place: 'Perfect Canandaigua Lake Retreat - Beautiful Sunrise Views!', vacation rental in Middlesex
Bogie's Place: 'Perfect Canandaigua Lake Retreat - Beautiful Sunrise Views!', vacation rental in Middlesex
Bogie's Place: 'Perfect Canandaigua Lake Retreat - Beautiful Sunrise Views!', vacation rental in Middlesex

Bogie's Place: 'Perfect Canandaigua Lake Retreat - Beautiful Sunrise Views!'

Rental Home
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Cheery, comfortable, well-equipped lakefront condo with spectacular views!, vacation rental in Middlesex
Cheery, comfortable, well-equipped lakefront condo with spectacular views!, vacation rental in Middlesex
Cheery, comfortable, well-equipped lakefront condo with spectacular views!, vacation rental in Middlesex

Cheery, comfortable, well-equipped lakefront condo with spectacular views!

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Near Bristol Mountain with private beach access, vacation rental in Middlesex
Near Bristol Mountain with private beach access, vacation rental in Middlesex
Near Bristol Mountain with private beach access, vacation rental in Middlesex

Near Bristol Mountain with private beach access

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Canandaigua Lake Cottage in the Woods, vacation rental in Middlesex
Canandaigua Lake Cottage in the Woods, vacation rental in Middlesex
Canandaigua Lake Cottage in the Woods, vacation rental in Middlesex

Canandaigua Lake Cottage in the Woods

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Glen Hollow: Luxury Living with Private Waterfall, vacation rental in Middlesex
Glen Hollow: Luxury Living with Private Waterfall, vacation rental in Middlesex
Glen Hollow: Luxury Living with Private Waterfall, vacation rental in Middlesex

Glen Hollow: Luxury Living with Private Waterfall

Rental Home
3 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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'Short Stop' Ranch Home in a Quiet FLX Village, vacation rental in Middlesex
'Short Stop' Ranch Home in a Quiet FLX Village, vacation rental in Middlesex
'Short Stop' Ranch Home in a Quiet FLX Village, vacation rental in Middlesex

'Short Stop' Ranch Home in a Quiet FLX Village

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Bopple Hill Lodge - Modern Cabin with Lake View, vacation rental in Middlesex
Bopple Hill Lodge - Modern Cabin with Lake View, vacation rental in Middlesex
Bopple Hill Lodge - Modern Cabin with Lake View, vacation rental in Middlesex

Bopple Hill Lodge - Modern Cabin with Lake View

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront All Season Retreat on Canandaigua Lake! (End Unit Condo), vacation rental in Middlesex
Waterfront All Season Retreat on Canandaigua Lake! (End Unit Condo), vacation rental in Middlesex
Waterfront All Season Retreat on Canandaigua Lake! (End Unit Condo), vacation rental in Middlesex

Waterfront All Season Retreat on Canandaigua Lake! (End Unit Condo)

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Scenic Canandaigua Lake House - 200' of private waterfront - Private wooded lot!, vacation rental in Middlesex
Scenic Canandaigua Lake House - 200' of private waterfront - Private wooded lot!, vacation rental in Middlesex
Scenic Canandaigua Lake House - 200' of private waterfront - Private wooded lot!, vacation rental in Middlesex

Scenic Canandaigua Lake House - 200' of private waterfront - Private wooded lot!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront two story condo, vacation rental in Middlesex
Waterfront two story condo, vacation rental in Middlesex
Waterfront two story condo, vacation rental in Middlesex

Waterfront two story condo

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lakeside Condo with plenty of amenities, vacation rental in Middlesex
Lakeside Condo with plenty of amenities, vacation rental in Middlesex
Lakeside Condo with plenty of amenities, vacation rental in Middlesex

Lakeside Condo with plenty of amenities

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Treetop Tiny House! Minutes from Canandaigua. Deluxe! Peaceful! FUN!, vacation rental in Middlesex
Treetop Tiny House! Minutes from Canandaigua. Deluxe! Peaceful! FUN!, vacation rental in Middlesex
Treetop Tiny House! Minutes from Canandaigua. Deluxe! Peaceful! FUN!, vacation rental in Middlesex

Treetop Tiny House! Minutes from Canandaigua. Deluxe! Peaceful! FUN!

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Brand New Modern Penthouse Condo! Beautiful Sunrises and Lake View!, vacation rental in Middlesex
Brand New Modern Penthouse Condo! Beautiful Sunrises and Lake View!, vacation rental in Middlesex
Brand New Modern Penthouse Condo! Beautiful Sunrises and Lake View!, vacation rental in Middlesex

Brand New Modern Penthouse Condo! Beautiful Sunrises and Lake View!

Condo/Apartment
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Cottage on the hillside of Bristol with breathtaking views of Canandaigua Lake., vacation rental in Middlesex
Cottage on the hillside of Bristol with breathtaking views of Canandaigua Lake., vacation rental in Middlesex
Cottage on the hillside of Bristol with breathtaking views of Canandaigua Lake., vacation rental in Middlesex

Cottage on the hillside of Bristol with breathtaking views of Canandaigua Lake.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Newly Renovated Rustic Home at Canandaigua Lake, vacation rental in Middlesex
Newly Renovated Rustic Home at Canandaigua Lake, vacation rental in Middlesex
Newly Renovated Rustic Home at Canandaigua Lake, vacation rental in Middlesex

Newly Renovated Rustic Home at Canandaigua Lake

Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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New Listing! Secluded Lakeside Cottage with Stunning Views & Hot Tub, vacation rental in Middlesex
New Listing! Secluded Lakeside Cottage with Stunning Views & Hot Tub, vacation rental in Middlesex
New Listing! Secluded Lakeside Cottage with Stunning Views & Hot Tub, vacation rental in Middlesex

New Listing! Secluded Lakeside Cottage with Stunning Views & Hot Tub

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Treehouse on Canandaigua Lake. Family Retreat on 2 acres Hot Tub,Dock, Hoist, vacation rental in Middlesex
The Treehouse on Canandaigua Lake. Family Retreat on 2 acres Hot Tub,Dock, Hoist, vacation rental in Middlesex
The Treehouse on Canandaigua Lake. Family Retreat on 2 acres Hot Tub,Dock, Hoist, vacation rental in Middlesex

The Treehouse on Canandaigua Lake. Family Retreat on 2 acres Hot Tub,Dock, Hoist

Rental Home
8 bedrooms
2 bathrooms
Sleeps 18
Match: Sleeps
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4 SEASON LAKEFRONT CONDO WITH BEST VIEW ON CANANDAIGUA LAKE, vacation rental in Middlesex
4 SEASON LAKEFRONT CONDO WITH BEST VIEW ON CANANDAIGUA LAKE, vacation rental in Middlesex
4 SEASON LAKEFRONT CONDO WITH BEST VIEW ON CANANDAIGUA LAKE, vacation rental in Middlesex

4 SEASON LAKEFRONT CONDO WITH BEST VIEW ON CANANDAIGUA LAKE

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Shale Point Beach: '200ft of Prime Canandaigua Lakefront!', vacation rental in Middlesex
Shale Point Beach: '200ft of Prime Canandaigua Lakefront!', vacation rental in Middlesex
Shale Point Beach: '200ft of Prime Canandaigua Lakefront!', vacation rental in Middlesex

Shale Point Beach: '200ft of Prime Canandaigua Lakefront!'

Rental Home
6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Lake A Lot: 'Charming and Modern - Beautiful Canandaigua Lake Home!', vacation rental in Middlesex
Lake A Lot: 'Charming and Modern - Beautiful Canandaigua Lake Home!', vacation rental in Middlesex
Lake A Lot: 'Charming and Modern - Beautiful Canandaigua Lake Home!', vacation rental in Middlesex

Lake A Lot: 'Charming and Modern - Beautiful Canandaigua Lake Home!'

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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