Seymour Vacation Rentals

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Browse Select Seymour Vacation Homes

Business or Weekend escape
9.6 out of 10, Exceptional, (22)
"Quaint basement studio with personal touches"
The price is CA $101
CA $182 total
includes taxes & fees
Oct 1 - Oct 2
Business or Weekend escape
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
9.4 out of 10, Exceptional, (10)
"Beautiful condo as advertised, great communication."
The price is CA $205
CA $388 total
includes taxes & fees
Sep 30 - Oct 1
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Lakeside luxury: beautiful, relaxing 4 bedroom home
10.0 out of 10, Exceptional, (13)
"This house was perfect for my group of 6 college friends. We hadn't gotten together in over 10 years and wanted to relax and catch up. The furniture and bedding were extremely comfortable, the kitchen had everything we could possibly need and more! Very spacious home with off-street parking for 6 cars. We loved it here!!! "
Lakeside luxury: beautiful, relaxing 4 bedroom home
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, (21)
"Great stay for 50th birthday "
Lakeview Estate - Chef's Kitchen - NYC Getaway
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
10.0 out of 10, Exceptional, (111)
"Had a quick work trip and wish we stayed longer! "
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
10.0 out of 10, Exceptional, (40)
"We had such a great time! The views are stunning and the house has everything you need to enjoy your stay. The host Kerry was so helpful; we had a small issue with the shower and she had a plumber over within the hour to resolve it. Can’t wait to come back next summer! "
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
Spacious 4-BR house in lake community with beach access and swim-in-place spa.
2.0 star property
Spacious 4-BR house in lake community with beach access and swim-in-place spa.
Sunny East Haven Home w/ Grill: Walk to Beaches!
2.0 star property
10.0 out of 10, Exceptional, (1)
Sunny East Haven Home w/ Grill: Walk to Beaches!
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (123)
"Our stay was incredible! The property was gorgeous- even with the home owners on property we barely saw them. We had full, private access to the backyard space- beach, pool, hot tub, fire pit, etc- all to ourselves. The property was clean and inviting and we will definitely go back. Everyone was so friendly and the area is picturesque. "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Cheerful 4 bedrooms residential house.
9.8 out of 10, Exceptional, (20)
"My friends and I stayed in Bridgeport for a weekend of music, and we had a great experience here! The owners were responsive and the place was exactly what we needed"
Cheerful 4 bedrooms residential house.
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
10.0 out of 10, Exceptional, (45)
"This house is beautiful and has everything you need, including a gorgeous view of the Sound. All communication was swift and easy. My family built some wonderful memories here this week!"
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Lakefront Home, Close to Mt Southington!
10.0 out of 10, Exceptional, (12)
"Staff very much enjoyed the atmosphere after long days of work. Wonderful Ownership. Thank you so much Susan!"
Lakefront Home, Close to Mt Southington!
Milford Oasis: 2BR, Wi-Fi, Near Walnut Beach
9.6 out of 10, Exceptional, (14)
"We loved our little cottage, it was a perfect size for us. The backyard was a great space for our grandkids to run around in, which was fun for them as well. It was close to family so we could easily have them over for the day. The owners were very kid an responded quickly to our questions also. We also met some of the neighbors who were a lot of fun too!"
Milford Oasis: 2BR, Wi-Fi, Near Walnut Beach
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
10.0 out of 10, Exceptional, (12)
"The house is huge and is very well equiped. Owners are very responsive to any questions or issues. Wonderful stay for the family."
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Heavenly Home in New Haven
8.8 out of 10, Excellent, (15)
"The property was prepared well and we enjoyed our stay. Thanks"
The price is CA $640
CA $827 total
includes taxes & fees
Sep 30 - Oct 1
Heavenly Home in New Haven
Home on the sound
8.6 out of 10, Excellent, (7)
"I really enjoyed staying here and the apartment was really nice. The only complaint I have is that there was a pair of underwear with poop stains in the dryer left. The silverware was also all dirty and sticky and had stains all over them"
Home on the sound
Catch some Zzz at Black Rock Harbor
10.0 out of 10, Exceptional, (11)
"Loved this modernized beach cottage. Walking distance to food and Bev as well as the beach. Quiet neighborhood. Perfect stay. "
Catch some Zzz at Black Rock Harbor
Cozy 2 bedroom home located minutes from downtown
9.6 out of 10, Exceptional, (21)
"This was my second stay here and it went very well, yet again. Alioune really knows how to take care of the guest and responds extremely quick to any questions that are sent. The place is great. Very close to everything you are going to need and has plenty of space. Very adequate number of bed/bathrooms. I can't say enough. I'll be staying here again when I'm traveling to New Haven. 5-stars."
Cozy 2 bedroom home located minutes from downtown
The W at Wildemere Beach
10.0 out of 10, Exceptional, (3)
"We enjoyed our stay at The W! The short walk to the beach was great! We loved the coffee maker and made delicious lattes each day! The kitchen was well equipped and the beds were comfortable."
The W at Wildemere Beach
Colonial steps from beach: 3BR, 2BA Oasis with Hot Tub
Colonial steps from beach: 3BR, 2BA Oasis with Hot Tub
Don't see what you're looking for?
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.
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Other property types in Seymour

New Haven Village Suites
3.0 star property
7.6 out of 10, Good, (1927)
"Excellent! Best kept secret in New Haven. My room was spacious. Lobby was beautiful and had coffee and breakfast. I would stay again, but you must have a car."
The price is CA $133
CA $153 total
includes taxes & fees
Oct 13 - Oct 14
New Haven Village Suites
Business or Weekend escape
9.6 out of 10, Exceptional, (22)
"Quaint basement studio with personal touches"
The price is CA $101
CA $182 total
includes taxes & fees
Oct 1 - Oct 2
Business or Weekend escape
DUNE Fairfield Beach
3.0 star property
8.8 out of 10, Excellent, (36)
"It was perfect exactly as pictured! Clean modern unit with everything you can need. The shower is amazing! Loved every bit of the place. Would totally be worth it to come back for a longer stay in one of the bigger units. The premium studio was perfect what I needed this time around. "
The price is CA $619
CA $786 total
includes taxes & fees
Sep 29 - Sep 30
DUNE Fairfield Beach
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.