A waterfall cascading over rocks into a river, surrounded by lush green trees.

Seymour Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Seymour vacation rentals

A modern kitchen with white cabinets, a black countertop, and a dining area with a table and chairs.

1. Private Apartment in Southbury 102

Private Apartment in Southbury 102
Southbury
9.0 out of 10, Wonderful, (6 reviews)
"Over all a great place. Nice to have everything on one floor. Dogs loved it. Some businesses in the building and everyone is friendly!"
United States
Debbie P.
The price is ￥21,492
￥45,372 total
includes taxes & fees
Sep 9 - Sep 10
Private Apartment in Southbury 102
A view through a window with a clear sky and lush greenery outside.

2. Private Apartment in Southbury 101

Private Apartment in Southbury 101
Southbury
9.6 out of 10, Exceptional, (7 reviews)
"The apartment was nice, big area, loved this rental."
United States
Marissa G.
The price is ￥19,431
￥42,692 total
includes taxes & fees
Aug 31 - Sep 1
Private Apartment in Southbury 101
A dining area with a long table, four chairs, a chandelier, and a painting on the wall.

3. Spacious 2 Bedroom apartment close to Yale Bowl

Spacious 2 Bedroom apartment close to Yale Bowl
West New Haven
9.6 out of 10, Exceptional, (79 reviews)
"Clean, thoughtful, safe. Great stay"
United States
Daniel S.
The price is ￥20,696
￥37,094 total
includes taxes & fees
Sep 5 - Sep 6
Spacious 2 Bedroom apartment close to Yale Bowl
A white house with a wooden staircase leading to a porch.

4. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (36 reviews)
"Everything was perfect and it's a great place to stay. Highly recommended and the folks there are A+."
United States
Bob
The price is ￥14,764
￥20,165 total
includes taxes & fees
Sep 22 - Sep 23
Cozy One Bedroom Apartment Centrally Located in Southbury
A house with a front porch, a garage, and a well-maintained lawn.

5. Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (7 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
The price is ￥23,880
￥56,715 total
includes taxes & fees
Aug 28 - Aug 29
Angelica’s safe haven @ west haven
A living room with a flat-screen TV mounted on the wall, a yellow armchair, a patterned rug, and various decorative items on shelves and side tables.

6. The Sicilian

The Sicilian
West New Haven
9.2 out of 10, Wonderful, (15 reviews)
"It was the perfect day and very convenient for our trip for our son’s graduation. Thank you for being so receptive and helpful."
United States
Michele B.
The price is ￥15,618
￥37,623 total
includes taxes & fees
Sep 2 - Sep 3
The Sicilian
A modern living room with hardwood flooring, a leather sofa, a round coffee table, and a wooden side table. There is a dining area with a table and chairs visible in the background.

7. Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Shelton
The price is ￥34,265
￥88,481 total
includes taxes & fees
Aug 31 - Sep 1
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
A cozy bedroom with a bed, two chairs, a small table, a radiator, and a window with blinds.

8. Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.

Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.
Dwight
9.0 out of 10, Wonderful, (4 reviews)
"Nice little apartment. Clean and well maintained."
United States
David
The price is ￥21,890
￥37,449 total
includes taxes & fees
Sep 13 - Sep 14
Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.
A bedroom with a bed, a blue sofa, a radiator, a window with blinds, a dreamcatcher, and a framed picture on the wall.

9. One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
9.0 out of 10, Wonderful, (2 reviews)
"We enjoyed our stay. The accommodations were clean and spacious and communication was quick and helpful. Would definitely come back!"
United States
Rosanne M.
The price is ￥12,418
￥29,524 total
includes taxes & fees
Sep 14 - Sep 15
One bedroom in United States of America, New Haven
A row of brownstone buildings with a central staircase leading to the second floor.

10. Bright Downtown Studio near Yale & East Rock!

Bright Downtown Studio near Yale & East Rock!
Downtown New Haven
9.2 out of 10, Wonderful, (16 reviews)
"Pretty close to Yale campus"
United States
Dongjian
The price is ￥17,194
￥39,084 total
includes taxes & fees
Aug 30 - Aug 31
Bright Downtown Studio near Yale & East Rock!
A cozy living room with a grey sofa, a coffee table with books and a vase of flowers, and bookshelves filled with books and decorative items.

11. Spacious Bohemian Nook

Spacious Bohemian Nook
West New Haven
8.4 out of 10, Very Good, (9 reviews)
"The place was incredibly clean. The instructions were clear for entering and locking up. Great experience! Thanks Dylan. "
United States
Andrew P.
The price is ￥19,900
￥43,223 total
includes taxes & fees
Sep 15 - Sep 16
Spacious Bohemian Nook

12. Bright Downtown New Haven Escape

Bright Downtown New Haven Escape
Downtown New Haven
9.8 out of 10, Exceptional, (6 reviews)
"In the heart of downtown New Haven and convenient to everything."
United States
Stewart C.
The price is ￥18,945
￥51,856 total
includes taxes & fees
Aug 28 - Aug 29
Bright Downtown New Haven Escape
A modern interior with a fireplace, seating area, and storage lockers.

13. Modern Studio Retreat

Modern Studio Retreat
Dwight
9.0 out of 10, Wonderful, (2 reviews)
"Should be more specific about the option to park on the property. I had to park a long ways away and only afterwards once I got into the apartment I saw the pass that I could’ve parked on the premises."
United States
Daniel
Modern Studio Retreat
A bedroom with a bed, a ceiling fan, a bedside table, a rug, and a window.

14. Downtown New Haven Escape

Downtown New Haven Escape
Dwight
8.0 out of 10, Very Good, (7 reviews)
"Good location, nice apartment with good amenities"
United States
Robert
The price is ￥21,890
￥40,155 total
includes taxes & fees
Sep 2 - Sep 3
Downtown New Haven Escape
A neatly made bed with a checkered blanket, white pillows, and a framed picture on the wall.

15. Yale Casa Verde Studio

Yale Casa Verde Studio
Dwight
9.2 out of 10, Wonderful, (14 reviews)
"We had a very nice stay here! The hosts were lovely and very communicative, and they were able to help us with any problems we had very quickly."
United States
Luke
The price is ￥12,736
￥29,890 total
includes taxes & fees
Aug 30 - Aug 31
Yale Casa Verde Studio

16. Cozy Stay by Little Italy & Wooster Street

Cozy Stay by Little Italy & Wooster Street
Mill River
9.4 out of 10, Exceptional, (3 reviews)
"Easy access to key areas, easy parking and neat and well appointed place as promised."
United States
Dheerendra P.
The price is ￥18,945
￥48,195 total
includes taxes & fees
Aug 28 - Aug 29
Cozy Stay by Little Italy & Wooster Street
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

17. All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
10.0 out of 10, Exceptional, (2 reviews)
"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."
United States
Nadine C.
The price is ￥18,786
￥47,076 total
includes taxes & fees
Aug 30 - Aug 31
All New Studio apartment in center of town
A conference room with a long wooden table, black chairs, a blue runner, a jar of candies, a small box, and a framed artwork on the wall.

18. Stocked home close to Yale, in Heart of New Haven

Stocked home close to Yale, in Heart of New Haven
Mill River
9.2 out of 10, Wonderful, (27 reviews)
"Great value very close to university. "
United States
Lawrence
The price is ￥20,059
￥36,202 total
includes taxes & fees
Sep 2 - Sep 3
Stocked home close to Yale, in Heart of New Haven

19. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Very nice! Clean and had everything you would need for a few nights away from home. I book again. "
United States
ALRUNDUS L.
The price is ￥18,786
￥47,076 total
includes taxes & fees
Aug 30 - Aug 31
All New 1BR with tons of Charm
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

Hilton Garden Inn Milford

Hilton Garden Inn Milford

8/10 Good
"We stayed here for two nights when we were getting our house renovated. It was on our short list of hotels that accepted dogs that were 75 or more pounds. We have two German shepherds. The hotel had a lot of outdoor space to walk the dogs and had poopy bags and garbage outside. The staff was very friendly. We were on the first floor and had easy access to an exit door a few hundred feet from my room to easily walk the dogs. There is a small gym that was nice that I used the treadmill at. There’s a pool right next to the gym that we did not use, but it looked nice and clean. The room was nice. For a standard room it was on the bigger side. It had a small refrigerator, Keurig, coffee machine, and microwave. The bed was comfortable, but not the most comfortable I’ve slept on. The pillows were not very comfortable. There was a nice desk and the air conditioning worked well. There were electrical outlets and USB chargers to charge your devices on one of the nightstands. The shower and bathroom were clean. The water pressure in the shower was OK. There was a lot of counter space on the vanity to put toiletries. The main thing I did not like was that when you turned the bathroom light on it had a really loud fan. It would’ve been nice if there were separate switches for the fan and light. The Room was clean. There is a restaurant that we had grilled chicken sandwiches at one night that were really good. Overall, a nice three star property."
allison 2-night trip
Posted 3 hours ago
Hilton Garden Inn Milford

Find out more about Seymour

Search for holiday rentals in Seymour on Expedia! You can easily find your home rentals, villas, holiday apartments in Seymour using one of the methods below:

  • View our selection of featured holiday rentals in Seymour
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  • Enter your travel dates to view the best deals on holiday rentals in Seymour while they last

Look no further and take a look at our great range of rental properties in Seymour!

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?

Charming Home in Seaside: This vacation home rental near Seymour is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Seymour?

Choose from 4 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 Beacon Falls Town Recreation Field and Indian Well State Park.

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.