Vacation rentals in Middlesex

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Top-rated vacation rentals in Middlesex

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Guest suite in Bloomfield

4.93 out of 5 average rating, 280 reviews

Farm House Suite 15 minutes from Canandaigua lake

Country location on a quiet road just minutes from Canandaigua Lake, and Bristol Mountain. Large farmhouse, with private suite including a huge great room (450 sf), wrap around screened-in porch. Please note that bedrooms and bath are upstairs. Geothermal heating/cooling. No full kitchen or downstairs sink available, only toaster oven, mini fridge, coffee maker (Keurig) with seating for 4 in section of great room. TV, fast Wifi for all your devices. Plenty of privacy and room to spread out.

Jun 6 – 13

$60 per night
Guest favorite

Home in Canandaigua

4.97 out of 5 average rating, 275 reviews

Walnut Pond Retreat-Private house & scenic grounds

Perfect getaway for nature lovers, or as an Artist's retreat. Pristine wooded hills, wildlife, greenery & fall foliage each in their season. Striking aquatic views of large manicured pond with water lilies to please Monet, and a dock from which to paint them. Diverse wild birds at established feeders & generally on the property. Wood burning fireplace inside & fire pit out. Full kitchen. Gas grill. Extra space. Laundry. Small library / reading room. 5 miles to nearest town. New Cable WiFi.

Dec 21 – 28

$124 per night
Guest favorite

Cottage in Canandaigua

4.93 out of 5 average rating, 160 reviews

Bristol Retreat Cottage, Creekside with Hot Tub

Rest and unwind at this unique, romantic getaway nestled in the beautiful Bristol Hills. Just minutes away from Bristol Ski Resort, Canandaigua and Honeoye Lake, this cozy 1 bedroom 1 bathroom cottage is one of our two homes available along the peacefully flowing Mill Creek. Take in the natural beauty from the large patio and hot tub. Indoors you'll enjoy the gas fireplace, complimentary wifi and smartTV. The full kitchen and bathroom are stocked with many amenities to help you enjoy your stay.

May 27 – Jun 3

$159 per night

Popular amenities for Middlesex vacation rentals

Other great vacation rentals in Middlesex

Guest favorite

Home in Penn Yan

4.92 out of 5 average rating, 150 reviews

Keuka Lake Hilltop Cottage

Dec 11 – 18

$106 per night
Superhost

Guest suite in Canandaigua

4.81 out of 5 average rating, 172 reviews

Windsong Lodge-Canandaigua Lake at BristolHarbour

May 17 – 24

$144 per night
Guest favorite

Home in Prattsburgh

4.99 out of 5 average rating, 178 reviews

Whispering Pines Getaway - Best value in the area!

Sep 27 – Oct 4

$129 per night
Guest favorite

Apartment in Naples

5.0 out of 5 average rating, 140 reviews

Holiday Acres... something for everyone all year

Mar 15 – 22

$130 per night
Guest favorite

Cottage in Canandaigua

4.82 out of 5 average rating, 174 reviews

Cottage with Canandaigua Lake Acces

Nov 30 – Dec 7

$113 per night
Guest favorite

Cottage in Hemlock

4.96 out of 5 average rating, 105 reviews

Cottage in Hemlock

Dec 4 – 11

$98 per night
Superhost

Cabin in Naples

4.82 out of 5 average rating, 369 reviews

East hill cabins #1

Jul 7 – 14

$80 per night
Guest favorite

Chalet in Canandaigua

4.97 out of 5 average rating, 211 reviews

The Johnson Chalet in Bristol/Canandaigua*HOT TUB*

Jun 14 – 21

$243 per night
Guest favorite

Cabin in Middlesex

4.98 out of 5 average rating, 45 reviews

Country cabin at Timbers' Edge

Apr 15 – 22

$109 per night
Guest favorite

Cabin in Middlesex

4.85 out of 5 average rating, 40 reviews

~ Sweet Pea ~The Little House ~

Apr 9 – 16

$149 per night
Guest favorite

Camper/RV in Rushville

4.94 out of 5 average rating, 63 reviews

Secluded camper with extra room to relax in

Mar 10 – 17

$85 per night
Guest favorite

Townhouse in Canandaigua

4.95 out of 5 average rating, 57 reviews

Townhouse Lake Access/10 min to Bristol Mountain

Dec 20 – 27

$109 per night

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