Best Vacation Homes in Middlesex County
House
3 Bedrooms
3 Baths
6 Guests
Fireplace/Heating
Air Conditioner
Internet
Child Friendly
£1,253/Night
7 Nights - £8,768
House
10.0(11 Reviews)
3 Bedrooms
2 Baths
6 Guests
1399.31 ft²
Oceanfront- Fireplace/Heating
Ocean View
Balcony/Terrace
£372/Night
7 Nights - £2,605
Bed & Breakfast
9.8(191 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
View
£244/Night
7 Nights - £1,709
House
4 Bedrooms
4 Baths
11 Guests
Hot Tub- Fireplace/Heating
Pet Friendly
Kitchen
£454/Night
7 Nights - £3,181
Apartment
10.0(3 Reviews)
2 Bedrooms
2 Baths
5 Guests
1097.92 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£359/Night
7 Nights - £2,513
New
House
4 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
£355/Night
7 Nights - £2,483
House
10.0(133 Reviews)
2 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Parking
£280/Night
7 Nights - £1,960
Cottage
10.0(81 Reviews)
1 Bedroom
1 Bath
2 Guests
420 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
£129/Night
7 Nights - £900
Middlesex County Luxury Rentals
Cottage
10.0(1 Review)
9 Bedrooms
6 Baths
16 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£2,154/Night
7 Nights - £15,076
House
10.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
3000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£2,012/Night
7 Nights - £14,085
House
10.0(2 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
£1,648/Night
7 Nights - £11,538
House
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
Pool- Balcony/Terrace
- Kitchen
£1,546/Night
7 Nights - £10,819
House
9.8(6 Reviews)
4 Bedrooms
3 Baths
10 Guests
2000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£1,335/Night
7 Nights - £9,348
House
9.8(37 Reviews)
3 Bedrooms
2 Baths
12 Guests
1100 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£1,316/Night
7 Nights - £9,213
House
10.0(5 Reviews)
7 Bedrooms
3 Baths
14 Guests
2200 ft²
Private Pool- Oceanfront
- Fireplace/Heating
- Pool
£1,231/Night
7 Nights - £8,615
House
10.0(6 Reviews)
6 Bedrooms
3 Baths
14 Guests
2438 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£1,097/Night
7 Nights - £7,681
Middlesex County Pet Friendly Vacation Rentals
House
10.0(54 Reviews)
2 Bedrooms
1 Bath
8 Guests
1800 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
£351/Night
7 Nights - £2,456
House
10.0(3 Reviews)
3 Bedrooms
3 Baths
8 Guests
2195.84 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£225/Night
7 Nights - £1,578
Cabin
9.6(151 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£154/Night
7 Nights - £1,079
House
10.0(46 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£384/Night
7 Nights - £2,688
House
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
721.18 ft²
- View
- Pet Friendly
- Parking
- Internet
£175/Night
7 Nights - £1,222
![Stunning Artisan Waterfall Escape [Walk to Downtown]](https://imgservice.rentbyowner.co.uk/640x287/stunning-artisan-waterf-us-chester-ha-3211062918-0.jpg)
House
10.0(44 Reviews)
2 Bedrooms
3 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£342/Night
7 Nights - £2,394
Cottage
10.0(22 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£222/Night
7 Nights - £1,556
Cottage
10.0(16 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£219/Night
7 Nights - £1,534
Middlesex County Large Vacation Homes
Apartment
1 Bedroom
1 Bath
30 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
£697/Night
7 Nights - £4,882
Bed & Breakfast
10.0(1 Review)
7 Bedrooms
5 Baths
14 Guests
406.87 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Parking
£166/Night
7 Nights - £1,163
House
10.0(152 Reviews)
3 Bedrooms
2 Baths
10 Guests
1960 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£452/Night
7 Nights - £3,166
House
10.0(1 Review)
1 Bedroom
4 Baths
15 Guests
- View
- Pet Friendly
- Parking
- Air Conditioner
£1,045/Night
7 Nights - £7,313
House
10.0(102 Reviews)
4 Bedrooms
2 Baths
10 Guests
2450 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£786/Night
7 Nights - £5,503
House
10.0(30 Reviews)
4 Bedrooms
3 Baths
12 Guests
2250 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£883/Night
7 Nights - £6,183
Cottage
10.0(24 Reviews)
6 Bedrooms
2 Baths
12 Guests
2000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£790/Night
7 Nights - £5,529
Cabin
10.0(24 Reviews)
5 Bedrooms
4 Baths
10 Guests
2500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
£574/Night
7 Nights - £4,021
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
East Haddam
Westbrook Center
Westbrook
Clinton
Killingworth
Cromwell
Middletown
Middlefield
East Hampton
Lake Pocotopaug
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!
- Wake up with Views of the Ocean
- 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
2. How many vacation rentals have private pools in Middlesex County?
There are 15 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 533 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
House
10.0(20 Reviews)
9 Bedrooms
8 Baths
16 Guests
7500 ft²
- Private Pool
- Hot Tub
Spa- Fireplace/Heating
£1,019/Night
7 Nights - £7,130
Villa
10.0(7 Reviews)
4 Bedrooms
2 Baths
10 Guests
3600 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
£1,077/Night
7 Nights - £7,538
House
10.0(7 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
£431/Night
7 Nights - £3,015
House
10.0(4 Reviews)
5 Bedrooms
2 Baths
9 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
£571/Night
7 Nights - £4,000
House
10.0(1 Review)
2 Bedrooms
1 Bath
6 Guests
850 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
£408/Night
7 Nights - £2,859
Resort
10.0(1 Review)
2 Baths
6 Guests
850 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
£408/Night
7 Nights - £2,859
Cottage
9.8(113 Reviews)
4 Bedrooms
1 Bath
8 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
£297/Night
7 Nights - £2,077
House
9.8(50 Reviews)
5 Bedrooms
5 Baths
14 Guests
4500 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
£990/Night
7 Nights - £6,927
