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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Seymour vacation rentals

A modern living room with a black sofa, white armchair, and a coffee table with a decorative centerpiece.

1. 191 Seymour, Ave. Derby · Spacious Renovated 3 bedroom near GriffinHospital

191 Seymour, Ave. Derby · Spacious Renovated 3 bedroom near GriffinHospital
Derby
8.6 out of 10, Excellent, (8 reviews)
"Great stay! Perfect location for my needs. Clean and inviting rental. Modern and well kept. Will stay again. "
United States
Bary B.
191 Seymour, Ave. Derby · Spacious Renovated 3 bedroom near GriffinHospital
A kitchen with white cabinets, a black refrigerator, a double sink, and a window overlooking a wooded area.

2. Serene Country Cottage

Serene Country Cottage
Woodbridge
8.0 out of 10, Very good, (11 reviews)
"We had a great one night stay here! The place is really cute, clean and comfortable. One of the greatest parts about the stay was the host, Trent. He was welcoming and VERY responsive to questions! "
United States
felicia
$189 nightly
The price is $214
Sep 28 - Sep 29
Total with taxes and fees
Serene Country Cottage
A sunroom with large windows, wicker furniture, and a ceiling fan.

3. Welcome to Dove Haven — a peaceful and stylish retreat in the heart of Westville. Relax in the private hot tub, enjoy cozy sun-filled spaces, and walk to charming cafés, top restaurants, and beautiful Edgewood Park. Minutes from Yale and downtown.

Welcome to Dove Haven — a peaceful and stylish retreat in the heart of Westville. Relax in the private hot tub, enjoy cozy sun-filled spaces, and walk to charming cafés, top restaurants, and beautiful Edgewood Park. Minutes from Yale and downtown.
West New Haven
10.0 out of 10, Exceptional, (16 reviews)
"Beautiful house, convenient location, great amenities, responsive host."
United States
Niels G.
Welcome to Dove Haven — a peaceful and stylish retreat in the heart of Westville. Relax in the private hot tub, enjoy cozy sun-filled spaces, and walk to charming cafés, top restaurants, and beautiful Edgewood Park. Minutes from Yale and downtown.
A dining area with a long table, four chairs, a chandelier, and a painting on the wall.

4. 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.
$184 nightly
The price is $208
Sep 28 - Sep 29
Total with taxes and fees
Spacious 2 Bedroom apartment close to Yale Bowl
A modern kitchen with white cabinets, stainless steel appliances, and a grey wooden floor.

5. Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
9.4 out of 10, Exceptional, (6 reviews)
"It was amazing , clean and awesome and good time"
United States
Michael
$260 nightly
The price is $294
Oct 1 - Oct 2
Total with taxes and fees
Private Apartment in Southbury 103
A house with a front porch, a garage, and a well-maintained lawn.

6. Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (8 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
$298 nightly
The price is $339
Sep 29 - Sep 30
Total with taxes and fees
Angelica’s safe haven @ west haven
A view through a window with a clear sky and lush greenery outside.

7. 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.
$268 nightly
The price is $304
Oct 19 - Oct 20
Total with taxes and fees
Private Apartment in Southbury 101
A white house with a wooden staircase leading to a porch.

8. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (37 reviews)
"Great place. Had everything we needed and was very clean."
United States
Niki B.
$108 nightly
The price is $121
Sep 27 - Sep 28
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury
A spacious living area with a sofa, a dining table, and a kitchen in the background.

9. #43- Modern Luxury Log Cabin Retreat - Fire Pit

#43- Modern Luxury Log Cabin Retreat - Fire Pit
Prospect
9.4 out of 10, Exceptional, (3 reviews)
"3.5 rounding up to 4. We had a good stay overall. I travel fairly often and tend to reserve 5 stars for places where every detail of the guest experience feels really thoughtfully considered. This home was comfortable and worked fine for our trip, but it felt a bit more basic compared to some other rentals I’ve stayed in."
United States
Lauren P.
$512 nightly
The price is $553
Oct 6 - Oct 7
Total with taxes and fees
#43- Modern Luxury Log Cabin Retreat - Fire Pit
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.

10. Spacious Bohemian Nook

Spacious Bohemian Nook
West New Haven
8.4 out of 10, Very good, (9 reviews)
"We had a good time. Did some relaxing, a little beachtime and ate some good food."
United States
Erin S.
$225 nightly
The price is $254
Sep 28 - Sep 29
Total with taxes and fees
Spacious Bohemian Nook
A room with a large window, wooden furniture, and a vase with a plant.

11. VintageGem: Prime East Rock 5 mins to Yale 5 beds

VintageGem: Prime East Rock 5 mins to Yale 5 beds
East Rock
8.6 out of 10, Excellent, (4 reviews)
"Great time with friends."
United States
Ianaliz R.
$381 nightly
The price is $432
Sep 29 - Sep 30
Total with taxes and fees
VintageGem: Prime East Rock 5 mins to Yale 5 beds
A two-story house with a porch, a front door with a wreath, and a small garden area.

12. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (8 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
$290 nightly
The price is $329
Oct 8 - Oct 9
Total with taxes and fees
Bear Retreat - 2-bedroom house in Waterbury
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

13. Stylish Westville Apartment near Yale Campus

Stylish Westville Apartment near Yale Campus
West New Haven
8.8 out of 10, Excellent, (3 reviews)
"Convenient location & hosts"
United States
Northeast C.
$217 nightly
The price is $246
Sep 27 - Sep 28
Total with taxes and fees
Stylish Westville Apartment near Yale Campus
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.

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

Stocked home close to Yale, in Heart of New Haven
Mill River
9.0 out of 10, Wonderful, (29 reviews)
"Great value very close to university. "
United States
Lawrence
$196 nightly
The price is $222
Sep 27 - Sep 28
Total with taxes and fees
Stocked home close to Yale, in Heart of New Haven
A covered porch with a wicker chair and a potted plant.

15. 3-bedroom house just walking distance from Yale and Downtown

3-bedroom house just walking distance from Yale and Downtown
Dixwell
10.0 out of 10, Exceptional, (6 reviews)
"Great stay!"
United States
Mark S.
$398 nightly
The price is $451
Sep 28 - Sep 29
Total with taxes and fees
3-bedroom house just walking distance from Yale and Downtown
A marina with multiple docks and boats, surrounded by residential buildings and greenery.

16. Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Fair Haven
9.8 out of 10, Exceptional, (16 reviews)
"A cozy pet and family-friendly property. Very spacious."
United States
Wallace R.
$293 nightly
The price is $318
Sep 28 - Sep 29
Total with taxes and fees
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
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.

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

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Shelton
$418 nightly
The price is $475
Sep 27 - Sep 28
Total with taxes and fees
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
A row of brownstone buildings with a central staircase leading to the second floor.

18. 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
$215 nightly
The price is $244
Sep 27 - Sep 28
Total with taxes and fees
Bright Downtown Studio near Yale & East Rock!
A modern building with large glass windows, a curved entrance, and a well-lit outdoor area with trees.

19. Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale

Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale
East Rock
10.0 out of 10, Exceptional, (11 reviews)
"Our 2 night stay was great. We were there for daughter's graduation from University of New Haven. Neighborhood was so quaint with lots of places to walk to. Place was very clean and accommodating. We would stay again!"
United States
Kathryn C.
$416 nightly
The price is $472
Sep 29 - Sep 30
Total with taxes and fees
Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale
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.

20. The Sicilian

The Sicilian
West New Haven
9.2 out of 10, Wonderful, (16 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.
$212 nightly
The price is $240
Sep 27 - Sep 28
Total with taxes and fees
The Sicilian
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

Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

10/10 Excellent
"Great experience again enjoy the location and quiet"
Herbert 2-night trip
Posted 2 hours ago
Motel 6 New Haven - Branford, CT

Find out more about Seymour

Everything you need to know about Seymour vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Seymour vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Seymour vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Seymour vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Seymour. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Seymour in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $152 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Seymour rentals

At Expedia, we put the best Seymour vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Seymour rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Seymour vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Seymour. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy: This vacation home rental near Seymour is located on the waterfront and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.