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Middlesex Holiday Rentals

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

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

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

Beautiful Timber-Frame Cottage - Canandaigua Lake

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Canandaigua Lake Getaway, holiday rental in Middlesex

Canandaigua Lake Getaway

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Ltd Availability; 2 Steps Access --4BR/3BA--110 Ft Flat Beachfront--Family Home, holiday rental in Middlesex

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

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Historic Post Office Cottage with shared Lake Access, holiday rental in Middlesex

Historic Post Office Cottage with shared Lake Access

4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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2 bedrooms, 1 Queen size sleeper sofa, 1 Bathroom - Sleeps 6, holiday rental in Middlesex

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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A Beautiful, Fully Furnished Log Cabin Overlooking Keuka Lake, holiday rental in Middlesex

A Beautiful, Fully Furnished Log Cabin Overlooking Keuka Lake

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Naples Valley Getaway, holiday rental in Middlesex

Naples Valley Getaway

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious Log Home Overlooking Canandaigua Lake!  Pet Friendly, Sleeps 12, holiday rental in Middlesex

Spacious Log Home Overlooking Canandaigua Lake! Pet Friendly, Sleeps 12

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Dramatic Views!  Nature's Wonderland. 5 Minutes from Bristol Mountain, holiday rental in Middlesex

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

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Paradise with  NEW Jacuzzi Spa!, holiday rental in Middlesex

Waterfront Paradise with NEW Jacuzzi Spa!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Heron Cove Sanctuary - Peace, Privacy & Beauty!, holiday rental in Middlesex

Heron Cove Sanctuary - Peace, Privacy & Beauty!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Private 3Bd3.5Ba w/Gorg Views of Canandaigua Lake!  <COVID-19 Book w/Confidence>, holiday rental in Middlesex

Private 3Bd3.5Ba w/Gorg Views of Canandaigua Lake! <COVID-19 Book w/Confidence>

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Scenic Post and Beam Home Overlooking Canandaigua Lake! Sleeps 10, holiday rental in Middlesex

Scenic Post and Beam Home Overlooking Canandaigua Lake! Sleeps 10

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Canandaigua Lake Million Dollar Lake Views And Sunsets!, holiday rental in Middlesex

Canandaigua Lake Million Dollar Lake Views And Sunsets!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Cabin- A Gorgeous Newly Renovated Waterfront Cabin, holiday rental in Middlesex

The Cabin- A Gorgeous Newly Renovated Waterfront Cabin

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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3 Bedroom Townhouse in scenic Bristol Harbor Village, holiday rental in Middlesex

3 Bedroom Townhouse in scenic Bristol Harbor Village

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Historic Home, Keuka Lake, Finger Lakes NY, holiday rental in Middlesex

Beautiful Historic Home, Keuka Lake, Finger Lakes NY

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Newly Renovated Rustic Cabin in the Heart of the Finger Lakes, holiday rental in Middlesex

Newly Renovated Rustic Cabin in the Heart of the Finger Lakes

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Two Darling Finger Lakes Region Cottages On The Shores of Canandaigua Lake Ny., holiday rental in Middlesex

Two Darling Finger Lakes Region Cottages On The Shores of Canandaigua Lake Ny.

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Canandaigua / Bristol Harbour Lakeside Condo -All Season Resort!, holiday rental in Middlesex

Canandaigua / Bristol Harbour Lakeside Condo -All Season Resort!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Breathtaking Canandaigua Lake Home In A Quiet Cove, holiday rental in Middlesex

Breathtaking Canandaigua Lake Home In A Quiet Cove

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Canandaigua Lake, Seneca Pt, Now with 4BR's en Suite sleeping 8, holiday rental in Middlesex

Canandaigua Lake, Seneca Pt, Now with 4BR's en Suite sleeping 8

4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Bristol View Lodge Mountainside, holiday rental in Middlesex

Bristol View Lodge Mountainside

7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Birch Lodge on Canandaigua Lake, holiday rental in Middlesex

Birch Lodge on Canandaigua Lake

5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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Private Farmhouse just minutes from Keuka Lake, on the Keuka Lake wine trail., holiday rental in Middlesex

Private Farmhouse just minutes from Keuka Lake, on the Keuka Lake wine trail.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Falling Waters Retreat, holiday rental in Middlesex

Falling Waters Retreat

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lakeview Lodge on Canandaigua Lake, holiday rental in Middlesex

Lakeview Lodge on Canandaigua Lake

12 bedrooms
5 bathrooms
Sleeps 24
Match: Sleeps
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Nature Lovers Getaway Nestled In The Hills Of The Finger Lakes Region.., holiday rental in Middlesex

Nature Lovers Getaway Nestled In The Hills Of The Finger Lakes Region..

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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The Birches-Peaceful resort retreat in finger lakes wine country, holiday rental in Middlesex

The Birches-Peaceful resort retreat in finger lakes wine country

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular 100 Acres On The Shores Of Canandaigua Lake, holiday rental in Middlesex

Spectacular 100 Acres On The Shores Of Canandaigua Lake

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Minutes from ski, golf, lake,weddings,concerts wine tours or just relax., holiday rental in Middlesex

Minutes from ski, golf, lake,weddings,concerts wine tours or just relax.

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming lake view home w/ easy lake access, full kitchen, and smart TV!, holiday rental in Middlesex

Charming lake view home w/ easy lake access, full kitchen, and smart TV!

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Chalet 64 Mountainside Retreat, holiday rental in Middlesex

Chalet 64 Mountainside Retreat

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Amazing Lakefront Cottage, Perfect Summer Getaway, holiday rental in Middlesex

Amazing Lakefront Cottage, Perfect Summer Getaway

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Serendipity - Peaceful Respite on Canandaigua Lake!, holiday rental in Middlesex

Serendipity - Peaceful Respite on Canandaigua Lake!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic Stone Farmhouse Recently Renovated, holiday rental in Middlesex

Historic Stone Farmhouse Recently Renovated

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Country house with private wooded setting and large yard, holiday rental in Middlesex

Country house with private wooded setting and large yard

6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Create Canandaigua Lakes Memories * Our Quaint Waterfront Getaway, holiday rental in Middlesex

Create Canandaigua Lakes Memories * Our Quaint Waterfront Getaway

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Clouds Rest, holiday rental in Middlesex

Clouds Rest

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Serene Cottage in Wine Country with Lake Access, holiday rental in Middlesex

Serene Cottage in Wine Country with Lake Access

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spend the Whole summer on Beautiful Canandaigua Lake, holiday rental in Middlesex

Spend the Whole summer on Beautiful Canandaigua Lake

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Home on the Lake! Enjoy your winter holidays!, holiday rental in Middlesex

Home on the Lake! Enjoy your winter holidays!

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Naples Cabin w/Large Wraparound Deck & Lake Views!, holiday rental in Middlesex

Naples Cabin w/Large Wraparound Deck & Lake Views!

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Evergreen Vista - Serene Country Estate in the Finger Lakes, holiday rental in Middlesex

Evergreen Vista - Serene Country Estate in the Finger Lakes

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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'The Grape Escape' Naples Home in NY Wine Country!, holiday rental in Middlesex

'The Grape Escape' Naples Home in NY Wine Country!

5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Canandaigua Lake House w/ Lake View & Fire Pit!, holiday rental in Middlesex

Canandaigua Lake House w/ Lake View & Fire Pit!

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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NEW! Luxe Finger Lakes Home w/ Home Gym, Game Room, holiday rental in Middlesex

NEW! Luxe Finger Lakes Home w/ Home Gym, Game Room

6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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NEW! Penn Yan Getaway w/ Spacious Deck & Yard!, holiday rental in Middlesex

NEW! Penn Yan Getaway w/ Spacious Deck & Yard!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Alpaca Farm Site, holiday rental in Middlesex

Tentrr Signature Site - Alpaca Farm Site

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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