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Top Holiday Rentals in Seymour

#1 views & private oceanfront estate featured in Coastal Living magazine!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Sean was a great host, was easy to communicate with and owns a beautiful house in a magical location. Rain or shine, there is something to do and he bent over backwards to make our stay perfect."
#1 views & private oceanfront estate featured in Coastal Living magazine!

New! Trail-side Haven Retreat! Pet friendly

9.4 out of 10, Exceptional, (8)
"Clean and comfortable, in a quiet area. Prefect for a family gathering"
The price is £265
includes taxes & fees
2 Jul - 3 Jul
New! Trail-side Haven Retreat! Pet friendly

Newly Remodeled 1-BR Close to Everything yet Very Private

10.0 out of 10, Exceptional, (8)
"Well maintained and clean property perfect for one or two people. Much better than a hotel stay."
The price is £218
includes taxes & fees
26 Jun - 27 Jun
Newly Remodeled 1-BR Close to Everything yet Very Private

Gorgeous beachfront house with hot tub

The price is £914
includes taxes & fees
13 Jul - 14 Jul
Gorgeous beachfront house with hot tub

The Jewel of The Cove - Historic Coastal Retreat

2.0 star property
10.0 out of 10, Exceptional, (2)
"A group of us stayed there for a work trip and it was the perfect situation for us. The beds were SO comfortable! The decor was vibe! Supplies were plenty. Towels were top quality. The fire pit was so fun to use on our last night in town. Very close to a beach so we could dip our toes in the ocean.There is an airport runway behind the property but the noise wasn’t terrible. "
The price is £475
includes taxes & fees
24 Jul - 25 Jul
The Jewel of The Cove - Historic Coastal Retreat

Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

The price is £475
includes taxes & fees
27 Jun - 28 Jun
Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

Clear LI Sound waterview, Wedding pics, Yale&Beach

10.0 out of 10, Exceptional, (5)
"Amazing location & views. House was pristine & had all amenities. Great park & dog walking path across the street"
The price is £730
includes taxes & fees
1 Jul - 2 Jul
Clear LI Sound waterview, Wedding pics, Yale&Beach

Beautiful cozy home w jacuzzi & dock for boat

The price is £499
includes taxes & fees
9 Jul - 10 Jul
Beautiful cozy home w jacuzzi & dock for boat

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

7.6 out of 10, Good, (5)
"This was a 2 month stay for us and was not equipped for longer term stays. Storage is a challenge. On the plus side, the host is responds quickly and helped with any issues we had. The location was great as we needed to be in a specific area."
The price is £231
includes taxes & fees
30 Jun - 1 Jul
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

9.6 out of 10, Exceptional, (13)
"The apartment was beautiful. One highlight for the children was the arcade game in the living room. The view of the water was striking from the living room and bedroom. The neighborhood was very quiet. Shakeema was a great host, easy to contact and she responds quickly. Thank you! I would recommend this VRBO to family and friends."
The price is £304
includes taxes & fees
26 Jun - 27 Jun
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Gorgeous Waterfront 2:1 - 2 houses in 1 building.

The price is £700
includes taxes & fees
7 Jul - 8 Jul
Gorgeous Waterfront 2:1 - 2 houses in 1 building.

Heavenly Home in New Haven /5 mins drive from Yale

9.0 out of 10, Wonderful, (19)
"The property was prepared well and we enjoyed our stay. Thanks"
The price is £768
includes taxes & fees
29 Jun - 30 Jun
Heavenly Home in New Haven /5 mins drive from Yale

Stocked home close to Yale, in Heart of New Haven

9.0 out of 10, Wonderful, (16)
"We loved our stay. It was just as expected and the host is responsive and friendly"
The price is £186
includes taxes & fees
6 Jul - 7 Jul
Stocked home close to Yale, in Heart of New Haven

Casa Soleada in East Rock |King Bed| Near DT and Yale SOM | Free parking

9.8 out of 10, Exceptional, (10)
"Beautiful and spacious home in lovely neighbourhood. We so enjoyed our brief stay. "
The price is £324
includes taxes & fees
1 Jul - 2 Jul
Casa Soleada in East Rock |King Bed| Near DT and Yale SOM | Free parking

Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free Parking

9.6 out of 10, Exceptional, (8)
"Property owner takes great care of the place. Instructions were easy to follow and the location was right down the road from the places we were going to. We would rent again if we ever come back to New Haven"
The price is £308
includes taxes & fees
1 Jul - 2 Jul
Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free Parking

Orange Oasis in East Rock |Free Parking| Near Yale and DT|Large Memory Foam Beds

9.0 out of 10, Wonderful, (8)
"the apartment was so beautiful, clean, and spacious! it was a great area to be in! the beds were SUPER comfortable as well, highlight of my trip!"
The price is £332
includes taxes & fees
26 Jun - 27 Jun
Orange Oasis in East Rock |Free Parking| Near Yale and DT|Large Memory Foam Beds

Chic 1-bedroom apartment with WiFi, fitness room in cool New Haven

The price is £194
includes taxes & fees
7 Jul - 8 Jul
Chic 1-bedroom apartment with WiFi, fitness room in cool New Haven

Westshore Luxury

8.0 out of 10, Very good, (1)
"We were visiting friends so wanted to rent a place for our family (2 adults, 2 children). This property is ideally located just outside of New Haven, walking distance to the beach, easy parking, spacious and beautiful on the inside. The only hiccup was the owner forgot to include the door code and we did not realized this would prevent entry to the place until late at night when we were ready to check in on the first day. My only suggestion for future renters is to make sure the code is included...
The price is £506
includes taxes & fees
8 Jul - 9 Jul
Westshore Luxury

The Santiago in Science Park at Yale New Haven

8.6 out of 10, Excellent, (7)
"The property had everything needed and was a short distance to so many campus sites. Would definitely stay again."
The price is £155
includes taxes & fees
8 Jul - 9 Jul
The Santiago in Science Park at Yale New Haven

3-bedroom house just walking distance from Yale and Downtown

The price is £310
includes taxes & fees
7 Jul - 8 Jul
3-bedroom house just walking distance from Yale and Downtown
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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Frequently asked questions

Are there holiday rentals in Seymour?

Yes, there are holiday rentals in Seymour close to Waterski Connecticut, or you can select a more secluded 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 holiday rentals that Seymour has to offer?

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub : This holiday home rental outside of Seymour is located on the beach, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself with a garden and 1 hot tub.

How many holiday rentals will I find in Seymour?

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

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 wider area, you’ll find Indian Well State Park and Yale Golf Course.

What are holiday rentals like in Seymour?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Seymour. Holiday rentals feature extras like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a small group gathering.