Best Vacation Homes in Middlesex
1200 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $484/Night
For 7 Nights US $3,388
1872.92 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Resort
- Private Beach
- Oceanfront
- Skiing
US $275/Night
For 7 Nights US $1,924
1900 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $379/Night
For 7 Nights US $2,653
1754.52 ft²
6 Guests
3 Bedrooms
2 Bathrooms
House
- Spa
- Fireplace/Heating
- Parking
US $557/Night
For 7 Nights US $3,899
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cabin
- Hot Tub
- Fireplace/Heating
- Ocean View
US $247/Night
For 7 Nights US $1,729
1113 ft²
6 Guests
3 Bedrooms
1 Bathroom
Ocean View
Condo
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $292/Night
For 7 Nights US $2,043
1100 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $377/Night
For 7 Nights US $2,638
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Ocean View
US $242/Night
For 7 Nights US $1,695
Middlesex Luxury Rentals
6500 ft²
24 Guests
6 Bedrooms
4 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $3,536/Night
For 7 Nights US $24,752
3735 ft²
16 Guests
8 Bedrooms
5 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $3,139/Night
For 7 Nights US $21,973
5349 ft²
12 Guests
6 Bedrooms
5 Bathrooms
Family Friendly
Cottage
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $2,581/Night
For 7 Nights US $18,067
3735.08 ft²
16 Guests
8 Bedrooms
5 Bathrooms
House
- Hot Tub
- Fireplace/Heating
- View
US $2,320/Night
For 7 Nights US $16,240
16 Guests
6 Bedrooms
3 Bathrooms
Group Friendly
RV Rental
- Child Friendly
- Bedding/Linens
- Designated Smoking Area
US $2,065/Night
For 7 Nights US $14,457
1 ft²
12 Guests
4 Bedrooms
3 Bathrooms
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,804/Night
For 7 Nights US $12,626
14 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $1,540/Night
For 7 Nights US $10,781
14 Guests
6 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $1,499/Night
For 7 Nights US $10,493
Middlesex Pet Friendly Vacation Rentals
975 ft²
8 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $224/Night
For 7 Nights US $1,568
1184.03 ft²
8 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $128/Night
For 7 Nights US $896
1100 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $353/Night
For 7 Nights US $2,470
3799.66 ft²
16 Guests
6 Bedrooms
5 Bathrooms
House
- Pool
- Balcony/Terrace
- View
US $1,093/Night
For 7 Nights US $7,651
1180 ft²
8 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $188/Night
For 7 Nights US $1,319
900 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $458/Night
For 7 Nights US $3,206
1150 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $179/Night
For 7 Nights US $1,251
980 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $160/Night
For 7 Nights US $1,119
Middlesex Large Vacation Homes
3250 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $734/Night
For 7 Nights US $5,138
1496.18 ft²
14 Guests
1 Bedroom
3 Bathrooms
Ocean View
House
- Private Beach
- Hot Tub
- Spa
US $1,133/Night
For 7 Nights US $7,929
1800 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
US $645/Night
For 7 Nights US $4,514
3153.83 ft²
16 Guests
7 Bedrooms
6 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $1,172/Night
For 7 Nights US $8,204
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $267/Night
For 7 Nights US $1,872
4400 ft²
8 Guests
5 Bedrooms
5 Bathrooms
Ocean View
Cabin
- Hot Tub
- Fireplace/Heating
- Pool
US $806/Night
For 7 Nights US $5,644
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $790/Night
For 7 Nights US $5,533
3826 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Spa
US $1,113/Night
For 7 Nights US $7,793
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.
Middlesex Vacation Rental Frequently Asked Questions
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!
- Private 3Bd3.5Ba w/Lake View, Pool, Hot Tub, 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 188 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
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $603/Night
For 7 Nights US $4,223
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Pool
- Balcony/Terrace
- View
US $281/Night
For 7 Nights US $1,968
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Pool
- Balcony/Terrace
- Kitchen
US $227/Night
For 7 Nights US $1,590
3879 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $652/Night
For 7 Nights US $4,564
3150 ft²
16 Guests
7 Bedrooms
6 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $2,142/Night
For 7 Nights US $14,991
2550 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Spa
- Fireplace/Heating
- Pool
US $634/Night
For 7 Nights US $4,436
6500 ft²
16 Guests
6 Bedrooms
10 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $1,526/Night
For 7 Nights US $10,679
3385 ft²
10 Guests
4 Bedrooms
5 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Lake View
US $925/Night
For 7 Nights US $6,472
