Best Vacation Homes in Middlesex County
6 Guests
3 Bedrooms
2 Bathrooms
House
- Air Conditioner
- Internet
- Child Friendly
GB £601/Night
For 7 Nights GB £4,206
1399.31 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
GB £371/Night
For 7 Nights GB £2,595
1 Bedroom
1 Bathroom
Ocean View
Bed & Breakfast
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
GB £164/Night
For 7 Nights GB £1,151
1000 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
GB £266/Night
For 7 Nights GB £1,864
1097.92 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
GB £219/Night
For 7 Nights GB £1,536
950 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
GB £203/Night
For 7 Nights GB £1,421
420 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Pet Friendly
- Kitchen
GB £128/Night
For 7 Nights GB £897
560 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- View
GB £157/Night
For 7 Nights GB £1,097
Middlesex County Luxury Rentals
16 Guests
9 Bedrooms
6 Bathrooms
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
GB £2,146/Night
For 7 Nights GB £15,023
12 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
GB £1,384/Night
For 7 Nights GB £9,689
2000 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
GB £1,331/Night
For 7 Nights GB £9,315
2200 ft²
14 Guests
7 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
GB £1,243/Night
For 7 Nights GB £8,701
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Kitchen
GB £1,235/Night
For 7 Nights GB £8,647
3600 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Hot Tub
- Fireplace/Heating
GB £1,206/Night
For 7 Nights GB £8,445
15 Guests
1 Bedroom
4 Bathrooms
House
- View
- Pet Friendly
- Parking
GB £1,041/Night
For 7 Nights GB £7,287
7500 ft²
16 Guests
9 Bedrooms
8 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Spa
GB £1,015/Night
For 7 Nights GB £7,105
Middlesex County Pet Friendly Vacation Rentals
1800 ft²
8 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
GB £346/Night
For 7 Nights GB £2,419
2195.84 ft²
8 Guests
3 Bedrooms
3 Bathrooms
House
- Oceanfront
- Fireplace/Heating
- Ocean View
GB £225/Night
For 7 Nights GB £1,573
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
GB £114/Night
For 7 Nights GB £797
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
GB £400/Night
For 7 Nights GB £2,800
218.87 ft²
22 Guests
10 Bedrooms
10 Bathrooms
Ocean View
Bed & Breakfast
- Oceanfront
- Fireplace/Heating
- Ocean View
GB £242/Night
For 7 Nights GB £1,697
![Stunning Artisan Waterfall Escape [Walk to Downtown]](https://imgservice.rentbyowner.co.uk/640x301/stunning-artisan-waterf-us-chester-ha-3211062918-0.jpg)
6 Guests
2 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
GB £253/Night
For 7 Nights GB £1,773
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
GB £189/Night
For 7 Nights GB £1,322
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
GB £316/Night
For 7 Nights GB £2,213
Middlesex County Large Vacation Homes
30 Guests
1 Bedroom
1 Bathroom
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
GB £695/Night
For 7 Nights GB £4,865
406.87 ft²
14 Guests
7 Bedrooms
5 Bathrooms
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Balcony/Terrace
- View
GB £118/Night
For 7 Nights GB £826
1960 ft²
10 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
GB £324/Night
For 7 Nights GB £2,272
277.71 ft²
10 Guests
11 Bedrooms
5 Bathrooms
Ocean View
Bed & Breakfast
- Oceanfront
- Fireplace/Heating
- Pool
GB £225/Night
For 7 Nights GB £1,574
2450 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
GB £607/Night
For 7 Nights GB £4,250
4500 ft²
14 Guests
5 Bedrooms
5 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
GB £801/Night
For 7 Nights GB £5,608
1100 ft²
12 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
GB £657/Night
For 7 Nights GB £4,597
2250 ft²
12 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
GB £865/Night
For 7 Nights GB £6,053
Why Choose Rent By Owner for your Middlesex County 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 County
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here depends on your preferences for weather and local events, ensuring your stay in this region aligns perfectly with your ideal vacation experience.
Peak Season Highlights
Summer (June to August)
During the warmest months, this area experiences peak visitation, making it ideal for enjoying outdoor activities and scenic views.
Average Temperature Daytime: around 75°F to 85°F - Nighttime: around 60°F to 65°F
Fall (September to November)
As the leaves change colors, visitors flock here to enjoy the vibrant foliage and crisp autumn air, perfect for exploring local attractions.
Average Temperature Daytime: around 65°F to 70°F - Nighttime: around 50°F to 55°F
Off-Season Highlights
Winter (December to February)
With colder weather and fewer tourists, this time offers a quieter experience and opportunities for cozy getaways and off-season exploration.
Average Temperature Daytime: around 35°F to 45°F - Nighttime: around 20°F to 30°F
Spring (March to May)
In early spring, the region begins to thaw, and fewer visitors arrive, making it a peaceful period to enjoy the area's natural beauty and emerging blooms.
Average Temperature Daytime: around 50°F to 60°F - Nighttime: around 35°F to 45°F
Weekly Weather Forecast for Middlesex County
How to Book Your Middlesex County 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 County
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 spacious outdoor seating areas perfect for relaxing and entertaining amid the natural surroundings.
- Take advantage of private or shared gardens that offer a peaceful setting to unwind in the fresh air.
- Make use of outdoor grills or barbecue stations to host delicious cookouts during your stay.
- Spend time on well-maintained patios or decks that provide scenic views of the surrounding landscape.
- Relax by inviting swimming pools or hot tubs available at many properties within this area.
- Explore nearby walking or biking trails directly accessible from your rental for outdoor adventures.
- Utilize outdoor fire pits or fireplaces ideal for cozy evenings under the stars in this picturesque destination.
Top Attractions Around Middlesex County
What attractions are nearby?
Here, you can explore a variety of outdoor activities, cultural experiences, and scenic attractions that make this destination an ideal spot for your next getaway in Middlesex County, Connecticut.
Family Activities
- Edward H. Murphy Waterfront Park: Enjoy a family picnic or take a leisurely stroll along the scenic shoreline in this popular waterfront park, perfect for relaxing outings in the region.
- Middlesex County Historical Society Museum: Discover local history through engaging exhibits and interactive displays that make learning fun for children and adults alike.
- Johnson's Pond Recreation Area: Spend quality time with outdoor activities such as fishing, kayaking, and swimming in this tranquil pond setting within the area.
- Connecticut River Museum: Experience hands-on exhibits and boat tours along the historic river, offering an educational adventure suitable for the whole family.
Adult Activities
- Visit the Gillette Castle State Park: Explore this historic site where you can enjoy scenic hikes and discover the unique architecture nestled within the region's natural beauty.
- Enjoy boating and fishing on the Connecticut River: Take advantage of the area's waterways for a relaxing day of boating, fishing, or simply unwinding along the tranquil shores.
- Discover local history at the Middlesex County Historical Society: Immerse yourself in the area's rich heritage through engaging exhibits and educational programs housed nearby.
- Experience fine dining in charming local restaurants: Savor delicious cuisine at establishments that highlight the region’s culinary flavors, perfect for a leisurely adult evening out in this destination.
Other Places to Stay in Middlesex County, CT
Old Saybrook
Saybrook Manor
Westbrook Center
Westbrook
East Haddam
Clinton
Killingworth
Middletown
Cromwell
Middlefield
Lake Pocotopaug
East Hampton
Middlesex County Travel Tips
How Can You Make the Most of Your Stay?
- Plan your visit during the local seasons: Timing your stay to coincide with the region’s seasonal events and weather can enhance your experience in Middlesex County, Connecticut.
- Explore nearby outdoor activities: Take advantage of the area’s scenic parks and waterfronts to enjoy recreational activities that showcase this destination’s natural beauty.
- Discover local dining and attractions: Sampling regional cuisine and visiting popular sites will give you a richer understanding of what makes this part of Connecticut unique.
- Book your vacation rentals in advance: Securing your accommodations early ensures you find the ideal property for a comfortable and convenient stay in this destination.
Transportation Options
- Amtrak Train Service: You can enjoy convenient rail travel connecting to major cities, making it easy to explore nearby regions from here.
- Connecticut Transit Buses: Local transit options provide affordable transportation within the area and to neighboring towns, simplifying your daily excursions.
- Private Shuttle Services: Private shuttles offer door-to-door transfers for added comfort and flexibility during your stay in this destination.
- Rental Cars: Renting a car gives you the freedom to explore the region at your own pace, with multiple rental agencies available nearby.
Local Customs Options
- Clam Shacking: In this area, clam shacking is a cherished tradition where locals harvest shellfish by hand during designated seasons, offering an authentic taste of regional coastal life.
- Seasonal Lantern Festivals: During certain times of the year, you might experience vibrant lantern festivals that celebrate local culture with illuminated displays and community gatherings.
- Historical Preservation Practices: Here, residents take pride in maintaining historical sites and traditions, reflecting the region's deep-rooted appreciation for its past.
- Community Seafood Celebrations: Throughout the year, the region hosts community events centered around fresh seafood, giving visitors a chance to enjoy local culinary customs firsthand.
Frequently Asked Questions About Middlesex County?
1. What are the top vacation rentals in Middlesex County?
There are a lot of options in Middlesex County. If you plan on staying in the Middlesex County 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 County:
- Classic Lake House w/private waterfront, 4 steps to water, FirePit/Kayaks/canoe
- Waterfront Retreat overlooking Long Island Sound w/gorgeous sunrises & sunsets!
- Luxury Waterfront Home-Still some availability for Summer 2026
- Cozy cottage near downtown Clinton, Marina & Hammonasset Park
- Cozy Cottage at The Cabins
- UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge
- Seasonal cottage rental,waterview
- Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults
- Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
- Spacious yard and view of Long Island Sound- walk to secluded beach!
2. How many vacation rentals have private pools in Middlesex County?
There are 14 vacation rentals with private pools near Middlesex County. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Middlesex County are best for families?
If you are looking for a family-friendly vacation home in Middlesex County, 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 County:
4. How many Rentbyowner vacation rentals are available in Middlesex County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 527 in the Middlesex County 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 County.
5. What is the cancellation policy for vacation rentals in Middlesex County, Connecticut?
Cancellation policies vary depending on the specific property listing. To ensure you understand the terms, please review the cancellation details provided in the listing or contact the property owner directly.
6. How do I confirm my booking for a vacation rental in Middlesex County?
Booking confirmation typically occurs after you complete the reservation process on the listing page and receive a confirmation email. For any additional verification, reach out to the property owner through the platform.
7. Are there any specific check-in or check-out requirements for rentals here?
Check-in and check-out procedures are outlined in each property’s listing. For detailed instructions or special requests, contact the owner prior to your arrival to ensure a smooth stay.
8. What amenities are usually included in vacation rentals around this destination?
Amenities vary by property, but most vacation rentals in the area offer essentials such as Wi-Fi, parking, kitchen facilities, and linens. Review the property's feature list for specific details.
9. Is it possible to modify or cancel my reservation if my plans change?
Modifications and cancellations depend on the individual property's policy. Please refer to the listing details or contact the owner directly to discuss your options.
Middlesex County Top Rated Vacation Rentals
600 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
GB £153/Night
For 7 Nights GB £1,073
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Pool
GB £415/Night
For 7 Nights GB £2,905
9 Guests
5 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
GB £569/Night
For 7 Nights GB £3,985
850 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Hot Tub
- Spa
- Fireplace/Heating
GB £407/Night
For 7 Nights GB £2,849
850 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Resort
- Hot Tub
- Spa
- Fireplace/Heating
GB £407/Night
For 7 Nights GB £2,849
8 Guests
4 Bedrooms
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Pool
GB £267/Night
For 7 Nights GB £1,869
3667 ft²
14 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
GB £548/Night
For 7 Nights GB £3,837
3500 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
GB £400/Night
For 7 Nights GB £2,802
