Seymour Holiday Rentals

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Holiday Rentals in Seymour

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (60)
"Incredible staff, friendly, helpful. "
DUNE Fairfield Beach

Business or Weekend escape

9.2 out of 10, Wonderful, (40)
"Very nice owner with great communication. "
The price is AU$229
includes taxes & fees
20 July - 21 July
Business or Weekend escape

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

10.0 out of 10, Exceptional, (1)
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (133)
"Perfect location for a get-away! Beautiful location on the water. The cottage was cozy & had everything we needed. Very clean. Lots to do in the area. Host was very nice We had a great time and will absolutely be back! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

9.0 out of 10, Wonderful, (7)
"This property is well maintained. Some amenities available that made our stay more enjoyable. My only issue was the amount of noise you could hear throughout the night.but once you're asleep it doesn't matter. "
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

Luxury Designer 2 bedroom+office/3bed vacation home.

9.4 out of 10, Exceptional, (20)
"Had a great stay!"
The price is AU$673
includes taxes & fees
31 July - 1 Aug
Luxury Designer 2 bedroom+office/3bed vacation home.

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

The price is AU$305
includes taxes & fees
28 July - 29 July
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Luxury Apartments by Hyatus at Pierpont

4.0 star property
9.4 out of 10, Exceptional, (18)
"Excellent location downtown and close to yale. A lot of complimentary amenities and activities. Very nice size rooms. A nice residential feel for a weeks stay."
Luxury Apartments by Hyatus at Pierpont

Cozy 3 bedroom minutes from Yale and the beach

Cozy 3 bedroom minutes from Yale and the beach

Minutes to Walnut Beach, newly renovated 3 bedroom home

10.0 out of 10, Exceptional, (5)
"Very nice place."
Minutes to Walnut Beach, newly renovated 3 bedroom home

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.6 out of 10, Exceptional, (50)
"Great location, great stay!"
Luxury Furnished Apartments by Hyatus Downtown at Yale

Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

10.0 out of 10, Exceptional, (25)
"The house was very clean and comfortable with really nice seating inside and out with great views of the lake. Our family really enjoyed"
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

Main Street Westport, walk to shops, dining, downtown

9.0 out of 10, Wonderful, (2)
"Beautiful home, great location, communicative hosts…A"
Main Street Westport, walk to shops, dining, downtown

Heavenly Home in New Haven /5 mins drive from Yale

9.0 out of 10, Wonderful, (19)
"Place was so cute and spacious. Owner was awesome too! Definitely recommend."
The price is AU$1,488
includes taxes & fees
20 July - 21 July
Heavenly Home in New Haven /5 mins drive from Yale

Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

10.0 out of 10, Exceptional, (4)
"Beautiful house to stay, perfect location to beach and the host Robert was wonderful! Will be staying here again on our next visit. "
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

10.0 out of 10, Exceptional, (79)
"We stayed for a birthday weekend with a few other couples and had a great time. There is plenty of space for everyone to spread out and each 'area' of the house is incredibly comfortable (especially the movie theater). If you need anything there are plenty of stores close by and the area is very safe. Overall, no complaints and would recommend to anyone looking for a getaway."
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

Bright Milford Beach House w/ Outdoor Shower

9.2 out of 10, Wonderful, (10)
"We had the best time! It was clean, good location, and the owner was wonderful! We even got to go the beach in December! We would definitely rent this place again!!"
Bright Milford Beach House w/ Outdoor Shower

4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy

10.0 out of 10, Exceptional, (32)
"We went for a family vacation and we had a great time - location is close to lots of great places - house was clean and very roomy"
4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy

Direct Waterfront Private Beach Escape

9.8 out of 10, Exceptional, (14)
"The house was great! Beautiful ocean front property with beachy vibes all throughout the neighborhood and interior of the home. The host was extremely clear on directions and provided amazing instructions. Very comfortable stay! "
Direct Waterfront Private Beach Escape
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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Top Seymour Hotel Reviews

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?

Business or Weekend escape: This holiday home rental outside of Seymour is equipped with a BBQ, air conditioning and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a microwave and a coffee maker.

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 Whittemore Glen State Park.

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.