Best Vacation Homes in Middlesex
Cottage
10.0(96 Reviews)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
Oceanfront
Hot Tub
Fireplace/Heating
Ocean View
AU $1,174/Night
7 Nights - AU $8,219
Resort
10.0(3 Reviews)
3 Baths
6 Guests
1872.92 ft²
Private Beach- Oceanfront
Skiing- Fireplace/Heating
AU $380/Night
7 Nights - AU $2,661
House
10.0(65 Reviews)
2 Bedrooms
1 Bath
6 Guests
1900 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
AU $539/Night
7 Nights - AU $3,775
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1754.52 ft²
Spa- Fireplace/Heating
Parking
Internet
AU $770/Night
7 Nights - AU $5,393
Cabin
10.0(40 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
Balcony/Terrace
AU $358/Night
7 Nights - AU $2,503
Condo
10.0(34 Reviews)
3 Bedrooms
1 Bath
6 Guests
1113 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
View
AU $432/Night
7 Nights - AU $3,022
Cottage
10.0(32 Reviews)
2 Bedrooms
1 Bath
6 Guests
1100 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
AU $521/Night
7 Nights - AU $3,649
Condo
10.0(19 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $696/Night
7 Nights - AU $4,870
Middlesex Luxury Rentals
House
10.0(122 Reviews)
6 Bedrooms
4 Baths
24 Guests
6500 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $4,891/Night
7 Nights - AU $34,235
House
10.0(1 Review)
8 Bedrooms
5 Baths
16 Guests
3735 ft²
- Fireplace/Heating
- Balcony/Terrace
Kitchen- Parking
AU $4,342/Night
7 Nights - AU $30,391
Cottage
6 Bedrooms
5 Baths
12 Guests
5349 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $3,570/Night
7 Nights - AU $24,989
House
8 Bedrooms
5 Baths
16 Guests
3735.08 ft²
- Hot Tub
- Fireplace/Heating
- View
Air Conditioner
AU $3,209/Night
7 Nights - AU $22,462
House
9.6(25 Reviews)
6 Bedrooms
3 Baths
14 Guests
6275 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $2,990/Night
7 Nights - AU $20,929
House
10.0(2 Reviews)
4 Bedrooms
4 Baths
22 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $2,668/Night
7 Nights - AU $18,678
House
10.0(12 Reviews)
6 Bedrooms
4 Baths
14 Guests
Private Pool- Oceanfront
- Hot Tub
- Fireplace/Heating
AU $2,515/Night
7 Nights - AU $17,602
Cottage
9.6(11 Reviews)
4 Bedrooms
3 Baths
12 Guests
1 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
AU $2,495/Night
7 Nights - AU $17,463
Middlesex Pet Friendly Vacation Rentals
Cabin
9.8(106 Reviews)
2 Bedrooms
1 Bath
8 Guests
975 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
AU $358/Night
7 Nights - AU $2,508
House
8.0(1 Review)
2 Bedrooms
1 Bath
8 Guests
1184.03 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
AU $177/Night
7 Nights - AU $1,239
Cottage
9.8(90 Reviews)
2 Bedrooms
1 Bath
6 Guests
1100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $488/Night
7 Nights - AU $3,416
House
6 Bedrooms
5 Baths
16 Guests
3799.66 ft²
Pool- Balcony/Terrace
- View
- Pet Friendly
AU $1,512/Night
7 Nights - AU $10,582
Cottage
9.8(8 Reviews)
2 Bedrooms
1 Bath
8 Guests
1180 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
AU $261/Night
7 Nights - AU $1,824
Cottage
9.0(227 Reviews)
2 Bedrooms
1 Bath
4 Guests
1150 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $322/Night
7 Nights - AU $2,256
Cottage
8.8(244 Reviews)
1 Bedroom
1 Bath
3 Guests
980 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $268/Night
7 Nights - AU $1,876
House
1 Bedroom
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $315/Night
7 Nights - AU $2,203
Middlesex Large Vacation Homes
House
10.0(52 Reviews)
4 Bedrooms
3 Baths
10 Guests
3250 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $1,015/Night
7 Nights - AU $7,107
House
7.5(2 Reviews)
1 Bedroom
3 Baths
14 Guests
1496.18 ft²
- Private Beach
- Hot Tub
- Spa
- Skiing
AU $1,345/Night
7 Nights - AU $9,412
House
10.0(42 Reviews)
4 Bedrooms
2 Baths
10 Guests
1800 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
AU $994/Night
7 Nights - AU $6,959
House
10.0(25 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $370/Night
7 Nights - AU $2,589
Cabin
10.0(22 Reviews)
5 Bedrooms
5 Baths
8 Guests
4400 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
AU $1,673/Night
7 Nights - AU $11,710
House
10.0(5 Reviews)
5 Bedrooms
3 Baths
10 Guests
3826 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
AU $1,840/Night
7 Nights - AU $12,880
House
10.0(5 Reviews)
6 Bedrooms
2 Baths
14 Guests
3110 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $1,486/Night
7 Nights - AU $10,400
RV Rental
10.0(3 Reviews)
6 Bedrooms
3 Baths
16 Guests
Child Friendly
Bedding/Linens
Designated Smoking Area
AU $2,361/Night
7 Nights - AU $16,526
Why Choose Rent By Owner for your Middlesex Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Middlesex
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, as seasonal variations in Middlesex, New York, influence the overall ambiance and availability of local vacation rentals.
Peak Season Highlights
Summer (June to August)
During the warm summer months, this destination sees an influx of visitors seeking outdoor activities and pleasant weather. It's an ideal time to explore the region's natural beauty while enjoying your stay.
Average Temperature Daytime: 75-85°F - Nighttime: 55-65°F
Fall (September to November)
Early fall offers mild temperatures and vibrant foliage, making it a popular season for scenic drives and outdoor exploration in the area. Vacation rentals are in high demand as travelers take advantage of the comfortable climate.
Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F
Off-Season Highlights
Winter (December to February)
The winter months bring cooler weather, with fewer visitors around. This quieter period provides a peaceful atmosphere for those looking to enjoy the region’s serene landscape and cozy accommodations.
Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
Spring (March to May)
Spring signifies the transition into warmer weather, though it can still be quite unpredictable. It’s a good time to find deals on vacation rentals while experiencing the area's emerging greenery and budding blooms.
Average Temperature Daytime: 50-60°F - Nighttime: 35-45°F
Weekly Weather Forecast for Middlesex
How to Book Your Middlesex Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Middlesex
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a spacious outdoor patio or deck ideal for relaxing or dining al fresco amidst the natural beauty of the area.
- Take advantage of a shared or private swimming pool, perfect for cooling off during warm summer days in this scenic region.
- Benefit from well-maintained gardens or landscaped yards that enhance your outdoor experience and provide picturesque views.
- Make use of outdoor grilling facilities to host cookouts while enjoying the peaceful surroundings nearby.
- Discover ample outdoor space for recreational activities such as lawn games or picnics within the property grounds.
- Explore nearby trails or pathways accessible directly from your rental, offering a great way to enjoy the area's natural environment.
- Relax in outdoor seating areas designed for soaking in the tranquility and scenic vistas unique to this destination.
Top Attractions Around Middlesex
What attractions are nearby?
Within this charming region, you can enjoy a variety of outdoor activities and local attractions that make your stay here truly memorable.
Family Activities
- Climbing and Hiking at the Middlesex County Nature Preserve: Enjoy outdoor adventures in this scenic preserve, perfect for exploring with your family through walking trails and nature walks.
- Middlesex County Fairgrounds Events: Experience local culture and entertainment by attending seasonal fairs and community events hosted here, engaging all ages.
- Visit to the Regional Historical Museum: Discover the area's rich history through interactive exhibits and educational programs designed for curious young minds and history buffs alike.
- Family Picnics at State Park: Relax and unwind in the nearby state park, where spacious picnic areas and playgrounds make it an ideal spot for a family outing in this region.
Adult Activities
- Wine Tasting Tours: Explore local wineries and sample regional wines, immersing yourself in the area's renowned viticulture scene.
- Art Galleries and Studios: Discover the vibrant arts community through visits to galleries and artist studios scattered throughout here.
- Nature Hikes and Outdoor Recreation: Enjoy scenic trails and outdoor activities amidst the natural beauty that surrounds this destination.
- Historic Landmarks and Museums: Delve into the region’s rich history by touring preserved landmarks and engaging with local exhibits.
Other Places to Stay in Middlesex, NY
Clarks Gully
Middlesex Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Nature: Dedicate time to discovering the region's natural beauty, making outdoor activities a memorable part of your stay.
- Plan Your Visit During Off-Peak Seasons: Visiting during less busy times can offer a more relaxed experience and better access to popular spots.
- Connect With Local Recommendations: Seek advice from hosts or locals to uncover hidden gems and authentic experiences in the area.
- Choose Well-Located Vacation Rentals: Select accommodations that provide easy access to the key attractions and scenic spots around here for convenience and enjoyment.
Transportation Options
- New York State Thruway (Interstate 90): This major highway provides convenient road access to the region, making it easy for you to explore surrounding towns and attractions in the area.
- Local Bus Service: Public bus options connect this destination with nearby cities and points of interest, offering an affordable transportation choice during your stay.
- Regional Train Services: Regional rail lines serve the area, providing a reliable mode of travel for visitors looking to explore beyond the immediate vicinity.
- Rental Car Agencies: Several car rental services operate locally, allowing you the flexibility to visit remote or less accessible parts of this region at your own pace.
Local Customs Options
- Local Farming Traditions: Embrace the area's agricultural roots by participating in seasonal farm activities and learning about local crop harvesting, a common custom here that reflects this destination's rural heritage.
- Community Festivals: Attend traditional festivals held throughout the year that celebrate regional history and culture, offering an authentic experience unique to this part of New York.
- Historic Preservation Practices: Respect local efforts to preserve historic buildings and landmarks, which are integral to maintaining the area's cultural identity and charm.
- Regional Cuisine Etiquette: Savor locally influenced dishes while observing customary dining manners that highlight the region’s culinary traditions and community values.
Frequently Asked Questions About Middlesex?
1. What are the top vacation rentals in Middlesex?
There are a lot of options in Middlesex. If you plan on staying in the Middlesex area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Middlesex:
- Waterfront, 138 ft Private Beach, Sunset, ADA friendly w elevator & Hot Tub
- Grey's Getaway Cabin# 3 Cabin is a Slice of heaven in Finger lakes region!
- Amazing cabin in the Finger Lakes! Hiking, wineries, restaurants.etc! Pets ok
- #1 Rated Amazing Canandaigua Lake/4 bed/3 bath/1750sqft.Rare End Unit!
- Lake View w/Pool, HotTub, & Fast Wi-Fi
- Private! Unique Lake Front Cottage. Heron Cove Sanctuary, Beauty & Peace!
- Paradise on the Lake
- Beautiful Timber-Frame Cottage - Canandaigua Lake
- Evergreen Vista - quiet country house in the Finger Lakes
- Naples Cabin w/Lake Views & Wraparound Deck!
2. How many vacation rentals have private pools in Middlesex?
There are 1 vacation rentals with private pools near Middlesex. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Middlesex are best for families?
If you are looking for a family-friendly vacation home in Middlesex, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Middlesex:
4. How many Rentbyowner vacation rentals are available in Middlesex?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 187 in the Middlesex area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Middlesex.
5. What is the cancellation policy for vacation rentals in Middlesex, New York?
Cancellation policies vary by listing. It is recommended that you review the specific cancellation terms outlined in each rental's listing details or contact the property owner directly for clarification.
6. How do I ensure the property I book in this region meets my needs?
You can filter your search based on amenities, property type, and guest reviews to find a vacation rental that best fits your preferences. Reading the listing descriptions carefully and reaching out to hosts with any questions can also help ensure it meets your expectations.
7. Are there any booking restrictions or minimum stay requirements for rentals here?
Yes, some properties may have minimum night requirements or booking restrictions during peak seasons or special events. Please check the individual listing details or contact the property owner for precise information.
8. What should I know about the payment process when booking a vacation rental in this area?
Payments are typically handled through the booking platform’s secure system. Be sure to review the payment schedule and any deposit requirements specified in the listing before completing your reservation.
9. Is it possible to modify or cancel my booking once it has been confirmed in Middlesex, New York?
Modification and cancellation policies depend on the individual host’s terms. To avoid issues, read the cancellation and modification policies carefully on the listing page or contact the property owner directly for assistance.
Middlesex Top Rated Vacation Rentals
House
10.0(98 Reviews)
3 Bedrooms
3 Baths
6 Guests
2006 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
AU $1,002/Night
7 Nights - AU $7,011
Bed & Breakfast
10.0(6 Reviews)
1 Bedroom
1 Bath
4 Guests
- Pool
- Balcony/Terrace
- View
Breakfast
AU $315/Night
7 Nights - AU $2,205
Bed & Breakfast
10.0(4 Reviews)
1 Bedroom
1 Bath
3 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Parking
AU $314/Night
7 Nights - AU $2,199
House
9.6(29 Reviews)
4 Bedrooms
3 Baths
8 Guests
3879 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $1,016/Night
7 Nights - AU $7,115
House
10.0(1 Review)
7 Bedrooms
6 Baths
16 Guests
3150 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
AU $2,962/Night
7 Nights - AU $20,734
House
9.8(8 Reviews)
4 Bedrooms
3 Baths
8 Guests
2550 ft²
- Spa
- Fireplace/Heating
- Pool
- Ocean View
AU $876/Night
7 Nights - AU $6,136
House
9.0(2 Reviews)
6 Bedrooms
10 Baths
16 Guests
6500 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
AU $2,110/Night
7 Nights - AU $14,770
House
6.0(1 Review)
4 Bedrooms
5 Baths
10 Guests
3385 ft²
- Fireplace/Heating
- Pool
Lake View- Balcony/Terrace
AU $1,279/Night
7 Nights - AU $8,952
