Vacation rentals in Middlesex

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Top-rated vacation rentals in Middlesex

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Guest favorite

Guest suite in Bloomfield

4.93 out of 5 average rating, 289 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.

Oct 6 – 13

G$14,469 GYD per night

Guest favorite

Home in Canandaigua

4.97 out of 5 average rating, 278 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.

Apr 4 – 11

G$29,512 GYD per night

Guest favorite

Cottage in Canandaigua

4.93 out of 5 average rating, 165 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.

Oct 7 – 14

G$37,723 GYD per night

Guest favorite

Guest suite in Penn Yan

4.95 out of 5 average rating, 145 reviews

Overlooking beautiful Keuka: Sunrise to Sunset!

A self-contained apt right in the heart of the beautiful Finger Lakes. Close to Keuka College, parks, restaurants, museums, trails, wineries, and kayak/bike rentals. Room for boats/trailers. Self-check in with lock box Super clean, lower apartment features a private entrance. It has a large bedroom with a comfortable king size bed, convertible to two twins, upon request. Twin/mattresses on floor can sleep up to 2 children ($15 ea) or 1 more adult($40)per night Private bathroom with shower.

May 8 – 15

G$24,133 GYD per night

Guest favorite

Condo in Canandaigua

5.0 out of 5 average rating, 106 reviews

Lakefront Retreat

Enjoy Gorgeous Panoramic Views of the Lake & surrounding Hillsides from the private & spacious balcony. PERMIT #2023-0075 Immaculate & Modern - 1 Bedroom 1 Bath condo, fully equipped Kitchen, Cozy Living Area, 70" TV with Netflix & Internet TV/Music Channels, use your streaming services etc. Leather Recliner, mesmerizing LED Fireplace , Very Comfortable King Bed, Washer, Dryer, Stylish Spa Bathroom and a Furnished Balcony w/ electric grill & a Finger Lakes View to Capture your Heart

Nov 23 – 30

G$43,742 GYD per night

Guest favorite

Guest suite in Naples

4.97 out of 5 average rating, 350 reviews

Sher's MILLION DOLLAR VIEW Artistic & Peaceful

Your newly decorated, 900 sq. ft. apartment comes complete with full kitchen, living room with wood burning stove, bedroom, private bath, and laundry room. You will love the amazing views on your 10 acre getaway including 2 ponds and hidden woods. Only a mile from the village of Naples, hiking trails, waterfalls, wine tastings, quaint shops, restaurants, golf course, leaf peeping, and only 15 min. to Bristol Mountain. Great for couples, solo adventurers, and business travelers.

Feb 10 – 17

G$23,909 GYD per night

Guest favorite

Home in Canandaigua

4.92 out of 5 average rating, 306 reviews

Maiden Lane Charm

Cozy updated cottage within walking distance and access to a private community beach. 2 bedrooms, fully equipped kitchen, bath and living space. This charming 800 sq foot home features a gas fire place to keep you cozy in the winter and an upper deck with lake view for relaxing in the warmer months. Large yard, partially fenced in, with play house for children. The storage shed houses outdoor games and wagon for the short trip (.3 miles) to the beach. 4 miles from CMAC.

Dec 29 – Jan 5

G$22,713 GYD per night

Guest favorite

Guest suite in Bloomfield

4.99 out of 5 average rating, 215 reviews

Finger Lakes 1 Bedroom Private Suite

This private 1 bedroom in-law style suite in the Bristol Hills has keyless entry, deck, bedroom, living area, bath with both shower and jetted tub and breakfast bar. The property is connected to the owners living area by locked door for your privacy and nestled on a back road in a rural area of the finger lakes. Views of the woods from all windows. If this room is booked, please check out our other listing on this property “Peaceful Finger Lakes Studio”

Sep 28 – Oct 5

G$18,436 GYD per night

Guest favorite

Cottage in Hemlock

4.96 out of 5 average rating, 109 reviews

Cottage in Hemlock

The peaceful atmosphere of this lovely home has everything you’ll need for a restful stay. Within a few miles of Hemlock, Canadice, Conesus, and Honeoye Lakes, enjoy canoeing, kayaking, fishing in the lakes or hiking, biking on the many nearby trails. Close to the Finger Lakes wine trails, local breweries, and distilleries. You’ll have the entire home to yourself. The bedroom has a queen size bed, and there are two self-inflating twin size air mattresses.

Apr 9 – 16

G$23,471 GYD per night

Guest favorite

Cabin in Branchport

4.94 out of 5 average rating, 162 reviews

Unique A-Frame Cabin in the Woods near Keuka Lake

This private A-Frame cabin is nestled on 10 acres of serene, wooded area with a large clearing - perfect for relaxing and playing outside! The small deck includes a gas grill and there is an established fire pit area with benches, so there are plenty of options for cooking and entertaining outdoors! Full -size shower and tub. One A/C unit in each bedroom and one on 1st floor. It's the perfect space for making wonderful memories with friends and family!

Dec 25 – Jan 1

G$26,018 GYD per night

Guest favorite

Bungalow in Geneva

4.9 out of 5 average rating, 165 reviews

1 Bedroom Bungalow on the Seneca Lake wine trail

Newly remodeled and fully outfitted bungalow, 3 miles from Geneva, across the road from Seneca Lake, and right in the heart of wine country. Peaceful country setting with the convenience of being near a bustling, walkable town, and two restaurants within a half mile. Owners affiliated with neighboring Roy’s Marina which offers access to kayak and boat rentals as well as launching and dry docking. Ideal for a weekend of wine and/or fishing.

Mar 13 – 20

G$23,562 GYD per night

Guest favorite

Cabin in Naples

4.86 out of 5 average rating, 521 reviews

Hi-Tor Hideaway. The Cure for Cabin Fever.

A beautiful log cabin in the woods with an incredible view, that sleeps 5. There is a queen bed downstairs, a double in loft and then a roll-away twin in living room. Peace and quiet, discovering nature and resetting yourself. Life has been a challenge and it is good to step back sometimes. Our peaceful retreat is centrally located near many parks and waterfalls. Located between beautiful Canandaigua, Keuka and Seneca Lakes.

Feb 22 – Mar 1

G$29,347 GYD per night