Seymour Vacation Rentals

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Vacation Rentals in Seymour

New Haven Village Suites
3.0 star property
7.6 out of 10, Good, 1,848 reviews
"We stayed only one night as planned. The property is in need of renovation, more than just paint. Our room had a musty smell and the carpets were worn out. The people working there were great. I hope they can rejuvenate this area. "
The price is CA $128
CA $148 total
includes taxes & fees
Jul 1 - Jul 2
New Haven Village Suites
Business or Weekend escape
9.4 out of 10, Exceptional, 15 reviews
"3rd time here. Very clean. Easy to communicate with the owner. A great place for a one day or more gateway."
The price is CA $103
CA $185 total
includes taxes & fees
Jun 23 - Jun 24
Business or Weekend escape
DUNE Fairfield Beach
3.0 star property
9.4 out of 10, Exceptional, 12 reviews
"perfectly clean, quiet, great location "
The price is CA $334
CA $460 total
includes taxes & fees
Jun 20 - Jun 21
DUNE Fairfield Beach
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, 113 reviews
"Was looking for a coastal retreat to enjoy a couple days with my daughter who lives near this location. This property had everything from a super clean, cozy studio with fridge and counters filled with surprising treats, incredible hot tub with lights in the trees, pool to cool off and little private beach to launch a paddlleboard and kayak, or hang out at night with a burn pit. If you are just a beach person and want toes in the sand and to swim in the ocean, this area is not for you....
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Luxury Designer 2 bedroom+office/3bed vacation home.
9.6 out of 10, Exceptional, 11 reviews
"This was a great place. Very clean. Much larger than the photos make it seem. Host was very responsive. Neighborhood was a bit sketchy but overall a very comfortable and nice stay. Very close to the Hartford Healthcare Amphitheater which is where we needed to go. Would definitely return and highly recommend!"
The price is CA $176
CA $541 total
includes taxes & fees
Jun 24 - Jun 25
Luxury Designer 2 bedroom+office/3bed vacation home.
Luxury Furnished Apartments by Hyatus Downtown at Yale
3.5 star property
10.0 out of 10, Exceptional, 22 reviews
"This was an amazing property to stay at. Super accommodating when we needed to extend our stay. Very clean and easy to check in and out of. They thought of everything even down to the toothpaste!"
Luxury Furnished Apartments by Hyatus Downtown at Yale
Westport Paradise With Every Amenity!
10.0 out of 10, Exceptional, 14 reviews
"The guest house was spacious and well appointed. The furnishings were very comfortable. The grounds at the house are beautiful. We thoroughly enjoyed our stay."
The price is CA $802
CA $1,153 total
includes taxes & fees
Jun 21 - Jun 22
Westport Paradise With Every Amenity!
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
9.8 out of 10, Exceptional, 21 reviews
"The property was as described and the living space was perfect for our visit. The deck and views are amazing. If staying at this property, you just need to be aware that it is very difficult getting luggage and groceries into the property. You have to go down a long flight of stairs, walk down a very steep driveway and then go down another flight of stairs. Once you are in, bedroom access requires that you go up or down additional stairs."
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
10.0 out of 10, Exceptional, 15 reviews
"Donna, the host, was absolutely wonderful. Very responsive. Cute beach bungalow. Very comfortable. Perfect for the three of us, 2 adults and 19 year old daughter. Would absolutely recommend."
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
Beautiful cozy rooms near hospital and down town area
8.0 out of 10, Very good, 11 reviews
"People were very nice and welcoming. Area looks questionable but the place itself is very comfortable, clean and enjoyable."
The price is CA $150
CA $338 total
includes taxes & fees
Jun 20 - Jun 21
Beautiful cozy rooms near hospital and down town area
gorgeous victorian direct ocean front single family six bedroom, ten rooms
10.0 out of 10, Exceptional, 51 reviews
"Wonderful host. Easy communication. Great house."
gorgeous victorian direct ocean front single family six bedroom, ten rooms
Waterfront Cottage in Branford
10.0 out of 10, Exceptional, 81 reviews
"Beautiful house in a beautiful location! We hope to return soon!"
Waterfront Cottage in Branford
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins
9.4 out of 10, Exceptional, 3 reviews
"The location of Ms. Jay's place is unbeatable! My group and I were in town for an event in the Total Mortgage Arena. The drive was 5 minutes max! Ms. Jay is great with communication. She was always available for any questions. The apartment is very homey, cozy and comfortable. Very nicely decorated and it has everything you might need. (We would just recommend some mirrors in the bedrooms). The place is next to a very busy street which there is always a lot of noise, especially at night. One...
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Tidal Time Estate with Heated Pool, Game Room, and Golf Cart
9.2 out of 10, Wonderful, 7 reviews
"We had a wonderful time in the house. House was super clean, new, big and beautiful. The only complaints we had during our stay was the pool and the neighbors. Apparently owner has been having trouble with it and it was a horrible green, swampy color the entire time we were there. Kids unfortunately didn't get to swim much it in cause it looked so gross. We had an ordeal with the neighbors one night and after many warnings to them, ended up having to call the police to have them stop with the...
Tidal Time Estate with Heated Pool, Game Room, and Golf Cart
NEW Luxury 1bd apt w/all the amenities @ Yale, Wooster Sq, DT New Haven. Pets ok
9.0 out of 10, Wonderful, 2 reviews
"What a great place! Location, location. Located on edge of Little Italy with great restaurants and bars. Our favorite was Zenellis. Less than 15 minute walk to downtown New Haven with lots of dining options. Take in the Trinity Bar nearby- great fun! Furniture was modest but adequate. Great kitchen."
The price is CA $203
CA $430 total
includes taxes & fees
Jun 23 - Jun 24
NEW Luxury 1bd apt w/all the amenities @ Yale, Wooster Sq, DT New Haven. Pets ok
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
10.0 out of 10, Exceptional, 12 reviews
"Stayed at Coastal Retreat for a weekend visit with son who attends Fairfield University, brought both sets of parents and teen daughter (ages ranging 73-16), plenty of room and able to enjoy a wonderful family dinner with son even in attendance. Wonderful area, close walk to beach and easy to get to downtown Fairfield and university. Very clean and welcoming! Greg was wonderful to work with and answered any question we had that came up both prior and upon arrival. The only thing we would mention...
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
Beautiful 4BR Beach House with Private Beach Access.
10.0 out of 10, Exceptional, 65 reviews
"Visited family back in CT and this was the perfect place to stay. Kind of like a Tardis, it was bigger on the inside! Thank you!"
Beautiful 4BR Beach House with Private Beach Access.
Direct Beachfront Property On Long Island Sound
10.0 out of 10, Exceptional, 26 reviews
"We had a wonderful time on the beach, in the ocean and just relaxing in the house. There were nice restaurants in the area to try and some fun day trips to take with the kids. We'd go back!"
Direct Beachfront Property On Long Island Sound
The Dream Location for Your Perfect Vacation
9.8 out of 10, Exceptional, 15 reviews
"The cottage has the most wonderful views! We loved our stay!"
The Dream Location for Your Perfect Vacation
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See all available properties in Seymour
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Seymour you may be interested in

New Haven Hotel
3.5 star property
8.8 out of 10, Excellent, 1,249 reviews
"We are visiting Yale. The location of the hotel is good -- walkable to the campus and business around. The room is clean and renovated."
The price is CA $204
CA $235 total
includes taxes & fees
Jun 23 - Jun 24
New Haven Hotel
Red Roof Inn Milford - New Haven
2.0 star property
7.0 out of 10, Good, 1,002 reviews
"Always my little spot to go to when pass through, it’s clean always and the atmosphere is clean!!"
The price is CA $114
CA $131 total
includes taxes & fees
Jun 23 - Jun 24
Red Roof Inn Milford - New Haven
The Circle Hotel Fairfield
3.0 star property
8.8 out of 10, Excellent, 1,131 reviews
"This hotel is a gem! "
The price is CA $172
CA $197 total
includes taxes & fees
Jun 27 - Jun 28
The Circle Hotel Fairfield
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Seymour. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Seymour?

Yes, there are vacation rentals in Seymour near Waterski Connecticut, or you can choose a more remote option if you're looking for a relaxing stay. Seymour is known for its restaurants and shopping. Make sure you have time to check out the beaches while you're in the area.

What are some of the best vacation home rentals in Seymour?

Business or Weekend escape: This vacation home rental near Seymour has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals will I find in Seymour?

Choose from 3 Expedia vacation rentals in Seymour for a memorable vacation.

What can I see and do in Seymour?

Family-friendly attractions include Waterski Connecticut, whereas Housatonic River is a spot to enjoy the outdoors. In the larger area, you’ll find Indian Well State Park and Southern Connecticut State University.

What are vacation rentals like in Seymour?

Vacation rentals are privately owned accommodations you can stay in for several days or longer in Seymour. Vacation rentals provide amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for small groups.

Recent reviews of Seymour properties
Expedia verified reviews