Middlesex Vacation Rentals & Ski-in/Ski-out Homes
Cabin
10.0Exceptional
(40 Reviews)
2 Bedrooms
1 Bath
6 Guests
Hot Tub
Fireplace/Heating
Ocean View
Balcony/Terrace
US $255/Night
7 Nights - US $1,787
Resort
- Rochester
- ·
- Canandaigua
- 7.09 mi to center
10.0Exceptional
(3 Reviews)
3 Baths
6 Guests
1872.92 ft²
Private Beach
Oceanfront
Skiing- Fireplace/Heating
US $275/Night
7 Nights - US $1,924
Condo
- Rochester
- ·
- Canandaigua
- 7.03 mi to center
10.0Exceptional
(34 Reviews)
3 Bedrooms
1 Bath
6 Guests
1113 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
View
US $400/Night
7 Nights - US $2,798
House
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1754.52 ft²
Spa- Fireplace/Heating
- Balcony/Terrace
Parking
US $557/Night
7 Nights - US $3,899
Cottage
10.0Exceptional
(32 Reviews)
2 Bedrooms
1 Bath
6 Guests
1100 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $377/Night
7 Nights - US $2,638
Condo
- Rochester
- ·
- Canandaigua
- 6.92 mi to center
10.0Exceptional
(24 Reviews)
3 Bedrooms
1 Bath
4 Guests
1100 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $254/Night
7 Nights - US $1,776
Condo
- Rochester
- ·
- Canandaigua
- 6.88 mi to center
10.0Exceptional
(20 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $494/Night
7 Nights - US $3,456
Condo
- Rochester
- ·
- Canandaigua
- 6.91 mi to center
10.0Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
4 Guests
1134 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $344/Night
7 Nights - US $2,411
RV Rental
10.0Exceptional
(10 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
Child Friendly
Security/Safety
US $228/Night
7 Nights - US $1,599
Luxury Places to Stay in Middlesex
Over 181+ Luxury Places to Stay in or Near Middlesex
House
10.0Exceptional
(122 Reviews)
6 Bedrooms
4 Baths
24 Guests
6500 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $3,824/Night
7 Nights - US $26,765
House
10.0Exceptional
(1 Review)
8 Bedrooms
5 Baths
16 Guests
3735 ft²
- Fireplace/Heating
- Balcony/Terrace
Kitchen- Parking
US $3,151/Night
7 Nights - US $22,057
Cottage
6 Bedrooms
5 Baths
12 Guests
5349 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $2,986/Night
7 Nights - US $20,900
House
- Rochester
- ·
- Grange Landing
- 0.61 mi to center
10.0Exceptional
(5 Reviews)
5 Bedrooms
3 Baths
10 Guests
3826 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
US $2,410/Night
7 Nights - US $16,869
House
8 Bedrooms
5 Baths
16 Guests
3735.08 ft²
- Hot Tub
- Fireplace/Heating
- View
Air Conditioner
US $2,320/Night
7 Nights - US $16,240
House
- Rochester
- ·
- Grange Landing
- 0.15 mi to center
6 Bedrooms
5 Baths
16 Guests
3799.66 ft²
Pool- Balcony/Terrace
- View
Pet Friendly
US $2,300/Night
7 Nights - US $16,100
House
- Rochester
- ·
- Grange Landing
- 0.15 mi to center
10.0Exceptional
(13 Reviews)
6 Bedrooms
4 Baths
14 Guests
Private Pool- Oceanfront
- Hot Tub
- Fireplace/Heating
US $2,160/Night
7 Nights - US $15,120
House
9.6Exceptional
(25 Reviews)
6 Bedrooms
4 Baths
14 Guests
6275 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $2,056/Night
7 Nights - US $14,389
House
10.0Exceptional
(2 Reviews)
6 Bedrooms
5 Baths
28 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,995/Night
7 Nights - US $13,962
Top-Rated Vacation Rentals with a Pool in Middlesex
Over 14+ Top-Rated Vacation Rentals with a Pool in or Near Middlesex
Cabin
10.0Exceptional
(26 Reviews)
5 Bedrooms
5 Baths
8 Guests
4400 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $1,164/Night
7 Nights - US $8,150
Bed & Breakfast
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
4 Guests
- Pool
- Balcony/Terrace
- View
Breakfast
US $228/Night
7 Nights - US $1,599
Bed & Breakfast
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
3 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $228/Night
7 Nights - US $1,594
House
9.6Exceptional
(30 Reviews)
4 Bedrooms
3 Baths
8 Guests
3879 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $744/Night
7 Nights - US $5,208
House
7 Bedrooms
6 Baths
16 Guests
3153.83 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Parking
US $1,172/Night
7 Nights - US $8,204
House
10.0Exceptional
(98 Reviews)
3 Bedrooms
3 Baths
6 Guests
2006 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $787/Night
7 Nights - US $5,509
House
- New York
- ·
- Branchport
- 1.69 mi to center
10.0Exceptional
(42 Reviews)
4 Bedrooms
2 Baths
10 Guests
1800 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $719/Night
7 Nights - US $5,031
House
10.0Exceptional
(1 Review)
7 Bedrooms
6 Baths
16 Guests
3150 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $2,142/Night
7 Nights - US $14,991
House
- Rochester
- ·
- Canandaigua
- 7.15 mi to center
9.8Exceptional
(8 Reviews)
4 Bedrooms
3 Baths
8 Guests
2550 ft²
- Spa
- Fireplace/Heating
- Pool
- Ocean View
US $634/Night
7 Nights - US $4,436
Pet-Friendly Vacation Rentals in Middlesex
Over 54+ Pet-Friendly Vacation Rentals in or Near Middlesex
Cottage
9.8Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
8 Guests
1180 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $351/Night
7 Nights - US $2,460
House
8.0Excellent
(1 Review)
2 Bedrooms
1 Bath
8 Guests
1184.03 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
Internet
US $128/Night
7 Nights - US $896
Cottage
9.0Exceptional
(230 Reviews)
2 Bedrooms
1 Bath
4 Guests
1150 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $194/Night
7 Nights - US $1,356
House
1 Bedroom
1 Bath
4 Guests
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $207/Night
7 Nights - US $1,449
House
- New York
- ·
- Branchport
- 2.53 mi to center
1 Bedroom
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $205/Night
7 Nights - US $1,433
New
Cabin
- New York
- ·
- Branchport
- 0.99 mi to center
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $405/Night
7 Nights - US $2,832
House
10.0Exceptional
(114 Reviews)
3 Bedrooms
1 Bath
8 Guests
1300 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $346/Night
7 Nights - US $2,423
House
10.0Exceptional
(32 Reviews)
3 Bedrooms
2 Baths
6 Guests
2000 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $981/Night
7 Nights - US $6,867
House
10.0Exceptional
(17 Reviews)
4 Bedrooms
1 Bath
8 Guests
1400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $664/Night
7 Nights - US $4,651
Large Vacation Homes & Villas in Middlesex
Over 38+ Large Vacation Homes & Villas in or Near Middlesex
House
10.0Exceptional
(5 Reviews)
6 Bedrooms
2 Baths
14 Guests
3110 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $1,227/Night
7 Nights - US $8,589
House
7.5Very Good
(2 Reviews)
5 Bedrooms
3 Baths
14 Guests
1496.18 ft²
- Private Beach
- Hot Tub
- Spa
- Skiing
US $760/Night
7 Nights - US $5,321
RV Rental
10.0Exceptional
(3 Reviews)
6 Bedrooms
3 Baths
16 Guests
- Child Friendly
Bedding/Linens
Designated Smoking Area
US $1,707/Night
7 Nights - US $11,948
Ski Chalet
10.0Exceptional
(3 Reviews)
5 Bedrooms
2 Baths
10 Guests
2732 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Balcony/Terrace
US $723/Night
7 Nights - US $5,062
House
10.0Exceptional
(2 Reviews)
4 Bedrooms
4 Baths
22 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,404/Night
7 Nights - US $9,828
House
9.8Exceptional
(10 Reviews)
5 Bedrooms
3 Baths
14 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,255/Night
7 Nights - US $8,785
House
9.8Exceptional
(9 Reviews)
5 Bedrooms
2 Baths
10 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,183/Night
7 Nights - US $8,278
House
- Rochester
- ·
- Grange Landing
- 0.38 mi to center
9.6Exceptional
(31 Reviews)
4 Bedrooms
3 Baths
11 Guests
1800 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $1,158/Night
7 Nights - US $8,106
Cottage
9.6Exceptional
(11 Reviews)
4 Bedrooms
3 Baths
12 Guests
1 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $1,787/Night
7 Nights - US $12,508
Wheelchair Accessible Vacation Homes in Middlesex
Over 3+ Wheelchair Accessible Vacation Homes in or Near Middlesex
House
4 Bedrooms
3 Baths
12 Guests
2500 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,105/Night
7 Nights - US $7,732
House
- Rochester
- ·
- Bristol Hills
- 2.55 mi to center
5.0Average
(3 Reviews)
3 Bedrooms
4 Baths
12 Guests
2786 ft²
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $554/Night
7 Nights - US $3,878
Condo
4.8Average
(6 Reviews)
3 Bedrooms
2 Baths
6 Guests
1638 ft²
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $182/Night
7 Nights - US $1,274
Middlesex Resorts and Airbnb Homes Under $200
Over 16+ Middlesex Resorts and Airbnb Homes Under $200
RV Rental
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Child Friendly
US $195/Night
7 Nights - US $1,364
House
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Pet Friendly
- Kitchen
- Child Friendly
Accessibility
US $191/Night
7 Nights - US $1,334
House
- Rochester
- ·
- Canandaigua
- 7.08 mi to center
9.8Exceptional
(65 Reviews)
2 Bedrooms
2 Baths
4 Guests
1560 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $137/Night
7 Nights - US $959
Cottage
8.8Fabulous
(245 Reviews)
1 Bedroom
1 Bath
3 Guests
980 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $198/Night
7 Nights - US $1,388
House
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $107/Night
7 Nights - US $750
Condo
- Rochester
- ·
- Canandaigua
- 7.22 mi to center
8.4Excellent
(5 Reviews)
3 Bedrooms
1 Bath
6 Guests
1638 ft²
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $188/Night
7 Nights - US $1,318
Condo
- Rochester
- ·
- Canandaigua
- 6.95 mi to center
3 Bedrooms
2 Baths
7 Guests
1500 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $191/Night
7 Nights - US $1,336
Condo
- Rochester
- ·
- Canandaigua
- 7.00 mi to center
9.6Exceptional
(37 Reviews)
3 Bedrooms
2 Baths
6 Guests
1416 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $168/Night
7 Nights - US $1,176
Condo
- Rochester
- ·
- Canandaigua
- 7.03 mi to center
9.6Exceptional
(21 Reviews)
3 Bedrooms
2 Baths
4 Guests
1113 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $183/Night
7 Nights - US $1,279
Instantly Bookable Vacation Homes in Middlesex
Over 80+ Instantly Bookable Vacation Homes in or Near Middlesex
House
10.0Exceptional
(8 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $749/Night
7 Nights - US $5,241
Ski Chalet
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $425/Night
7 Nights - US $2,975
House
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $231/Night
7 Nights - US $1,618
Condo
- Rochester
- ·
- Canandaigua
- 6.74 mi to center
9.8Exceptional
(7 Reviews)
2 Bedrooms
2 Baths
4 Guests
1410 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $300/Night
7 Nights - US $2,102
House
9.4Exceptional
(10 Reviews)
1 Bedroom
1 Bath
6 Guests
1200 ft²
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $309/Night
7 Nights - US $2,164
House
- Rochester
- ·
- Canandaigua
- 7.13 mi to center
9.4Exceptional
(8 Reviews)
2 Bedrooms
2 Baths
4 Guests
1250 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $295/Night
7 Nights - US $2,062
RV Rental
9.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Breakfast
- Child Friendly
Barbecue/Outdoor Cooking
US $228/Night
7 Nights - US $1,599
RV Rental
9.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Child Friendly
US $228/Night
7 Nights - US $1,599
House
2.0Average
(1 Review)
1 Bedroom
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Kitchen
US $386/Night
7 Nights - US $2,702
Book a Last Minute Place to Stay in Middlesex
About Middlesex Vacation Rentals
Explore over 190 vacation rentals in Middlesex with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Middlesex for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Middlesex. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Middlesex tailored to your preferences. On average, these rentals offer 1434.37 ft² of space, and are priced at an average of US $635 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Middlesex at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
Show more
Show less
Top Types of Ski Accommodations in Middlesex
| Type | Count |
|---|---|
| Vacation Homes | 108 |
| Cottages | 23 |
| Cabin Rentals | 19 |
| Unique Vacation Rentals | 5 |
| Ski Chalet Rentals | 5 |
| Holiday Apartments | 3 |
| B&B | 2 |
| Others | 1 |
Use these Quick Filters to Find a Vacation Rental in Middlesex
★ Pro Tip: Discover Your Ideal Vacation Rental in Middlesex with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
Weather in Middlesex, NY
View the weather forecast for Middlesex before booking your Middlesex Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Middlesex, NY
Sunski offers a large selection of top attractions around Middlesex . Research things to do on your vacation before you visit Middlesex.
Frequently Asked Questions About Middlesex?
What are the top vacation rentals in Middlesex?
When organizing your trip to Middlesex, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Middlesex. Peruse our collection of highly-rated properties and secure your reservation today.
- Waterfront, 138 ft Private Beach, Sunset, ADA friendly w elevator & Hot Tub
- Amazing cabin in the Finger Lakes! Hiking, wineries, restaurants.etc! Pets ok
- Cozy Country Cabin near Canandaigua-HOT TUB-Beautiful Sunsets-Close to CMAC
- Private getaway cabin in the woods
- Waterfront two story condo
- The Chosen Spot: Secluded, Views, Wineries, Hot tub, Skiing, Pet friendly!
- Sycamore Landing - Casual Lakefront Living at It's Best!
- 3 bedroom Lakeview home with New Hot tub!
- Braeloch Lodge - Canandaigua lakefront timberframe w/breathtaking views, spa
- Lakeside Condo with plenty of amenities near Bristol Mountain. Permit -2024-0018
How many vacation rentals have private pools in Middlesex?
Uncover 2 vacation rentals boasting private pools near Middlesex. Explore top-rated RBO homes offering access to a swimming pool:
- Mountain Top Manor - Pool - Hot Tub - Sleeps 16
- Cozy FLX Getaway with Pool, Close to Wineries and Lake
Which vacation homes or resorts in Middlesex are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Middlesex. Enjoy great views, locations and save money with SunSki Resorts.™
- Lakehouse with spectacular views on Canandaigua!
- Lakeside Condo with plenty of amenities close to Bristol Mountain - permit - 2024-0018
- The Overlook Couples Tiny Cabin-HotTub-Firepit. Best view in the Finger Lakes!
How many SunSkiResorts vacation rentals or resorts are available in Middlesex?
Discover the ideal vacation rental in Middlesex with SunSki Resorts™. We provide an extensive selection of over 190 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Middlesex.
People Also Ask
Finding the best prices in Middlesex
Map
