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, 285 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.

Aug 7 – 14

R1,319 ZAR per night

Guest favorite

Home in Canandaigua

4.97 out of 5 average rating, 277 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.

Jan 23 – 30

R2,690 ZAR 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.

Mar 25 – Apr 1

R2,200 ZAR per night

Guest favorite

Condo in Canandaigua

5.0 out of 5 average rating, 104 reviews

Lakefront Retreat

Enjoy Gorgeous Panoramic Views of the Lake & surrounding hillsides from the private & spacious balcony. PERMIT #2021-0066 Immaculate & Modern - 1 Bedroom & 1 Bath condo, fully equipped Kitchen, Cozy Living Area, 70" TV with Netflix, Amazon Prime & Internet TV & Music Channels etc. Leather Recliner, mesmerizing LED Fireplace , Very Comfortable King Bed & large Closet. Washer, Dryer, Stylish Spa Bathroom and a Fully setup Balcony w/ electric grill & a View to Capture your Heart.

Nov 10 – 17

R3,931 ZAR per night

Guest favorite

Cottage in Naples

4.95 out of 5 average rating, 129 reviews

Hook, Wine and Sinker

Completely updated in 2022! Canandaigua lakefront 5 minutes outside of Naples, NY! Level lakefront- Stunning views of South Hill- perfect for autumn leaf gazing and also summertime swims off the permanent dock. With kayak, inflatable toys, gas BBQ, WiFi, cable TV & electric awning over a picnic table. Enjoy s’mores over the campfire pit. Tastefully decorated, well equipped kitchen, washer/dryer & bedroom AC. Escape to the vineyards, Bristol Mtn. & all the Finger Lakes has to offer!

Oct 22 – 29

R7,630 ZAR 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 2 – 9

R2,179 ZAR per night

Guest favorite

Home in Canandaigua

4.93 out of 5 average rating, 304 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.

Oct 16 – 23

R2,083 ZAR per night

Guest favorite

Guest suite in Bloomfield

4.99 out of 5 average rating, 213 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”

Oct 5 – 12

R1,683 ZAR 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!

Aug 29 – Sep 5

R2,692 ZAR per night

Guest favorite

Cabin in Naples

4.86 out of 5 average rating, 520 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.

Dec 4 – 11

R2,675 ZAR per night

Guest favorite

Cabin in Bloomfield

4.93 out of 5 average rating, 251 reviews

Relaxing Getaway Cabin...Explore The Finger Lakes!

Just 11 mile from Bristol Mountain, this unique cabin sits on top of a hill overlooking 100 acers of woods and fields. Relax and enjoy everything the cabin and property have to offer with 2.5 miles of walking trails, a large back deck, two fire pits and much more. Located in the Finger lakes Region offers easy access to many wineries, breweries, distilleries, antique stores, and shops. Rochester is 25 miles away and Victor is 8 miles.

Feb 10 – 17

R2,024 ZAR per night

Guest favorite

Guest suite in Naples

4.95 out of 5 average rating, 237 reviews

All Seasons Base Camp - Finger Lakes

**King sized bed; Private Entrance; Keurig Coffee Machine; Roku TV; Mini Fridge; Microwave; Toaster Oven; Walk to Main Street, restaurants, wineries, distillery and breweries** All Seasons Base Camp is perfect for a couple or 2 friends looking for a comfortable and convenient place to stay while visiting the Finger Lakes Region for hiking, biking, fishing, skiing, water falls chasing, and wine tasting!

Jun 12 – 19

R1,565 ZAR per night