Seymour Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
13 Jan - 14 Jan
Tomorrow
14 Jan - 15 Jan
This weekend
16 Jan - 18 Jan
Next weekend
23 Jan - 25 Jan

Our top choices for Seymour holiday rentals

Interior
Westville Stay • 2BR • Near Yale • Free Parking

Westville Stay • 2BR • Near Yale • Free Parking

Westville Stay • 2BR • Near Yale • Free Parking
West New Haven
10.0 out of 10, Exceptional, (3 reviews)
"We were only here for a short stay, but everything was smooth and comfortable for us! Hotel-like linens and blackout curtains made for a very cozy sleeping experience."
United States
ross f.
The price is HK$546
HK$1,707 total
includes taxes & fees
14 Jan - 15 Jan
Westville Stay • 2BR • Near Yale • Free Parking
Interior
Beach Apartment in Woodmont Milford

Beach Apartment in Woodmont Milford

Beach Apartment in Woodmont Milford
2.0 star property
Milford
9.0 out of 10, Wonderful, (2 reviews)
"Had a great stay!"
United States
Garry G.
The price is HK$998
HK$2,960 total
includes taxes & fees
18 Jan - 19 Jan
Beach Apartment in Woodmont Milford
Smart TV
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.2 out of 10, Wonderful, (15 reviews)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is HK$660
HK$1,273 total
includes taxes & fees
14 Jan - 15 Jan
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Fridge, microwave, oven, stovetop
Private Apartment in Southbury 103

Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
10.0 out of 10, Exceptional, (2 reviews)
"Property management team was very quick to respond to any question or issue I had. Excellent location around eateries and activities "
United States
Dominick S.
The price is HK$538
HK$1,760 total
includes taxes & fees
14 Jan - 15 Jan
Private Apartment in Southbury 103
Exterior
Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (21 reviews)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is HK$717
HK$981 total
includes taxes & fees
19 Jan - 20 Jan
Cozy One Bedroom Apartment Centrally Located in Southbury
Outdoor dining
Golden Gem in the Heart of East Rock | Cozy Comfortable 3BR Near DT | Yale

Golden Gem in the Heart of East Rock | Cozy Comfortable 3BR Near DT | Yale

Golden Gem in the Heart of East Rock | Cozy Comfortable 3BR Near DT | Yale
East Rock
9.4 out of 10, Exceptional, (3 reviews)
"Great time with friends."
United States
Ianaliz R.
The price is HK$897
HK$2,641 total
includes taxes & fees
14 Jan - 15 Jan
Golden Gem in the Heart of East Rock | Cozy Comfortable 3BR Near DT | Yale
Iron/ironing board, free WiFi, bed sheets
DUNE Fairfield Beach

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (78 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach
Interior
The ARLO - Walk to Brewery and Restaurants

The ARLO - Walk to Brewery and Restaurants

The ARLO - Walk to Brewery and Restaurants
Milford
9.4 out of 10, Exceptional, (3 reviews)
"Very nice house....loved the front enclosed porch, and the kitchen was amazing with everything we needed. The deck with the Blackstone Grill was a great place to sit and relax. We enjoyed many of the nearby restaurants too. Matt and Jess were great hosts!J&J, Mooresville, NC"
United States
Jena
The price is HK$702
HK$2,394 total
includes taxes & fees
14 Jan - 15 Jan
The ARLO - Walk to Brewery and Restaurants
Exterior
Charming Studio| Near Yale| Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven
Downtown New Haven
9.0 out of 10, Wonderful, (12 reviews)
"Great location, exactly as advertised. The shades are somewhat translucent, so a bit bright at night, but wore a mask and it was fine. "
United States
Scott B.
The price is HK$452
HK$1,325 total
includes taxes & fees
14 Jan - 15 Jan
Charming Studio| Near Yale| Downtown New Haven
Fridge, microwave, oven, stovetop
Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (2 reviews)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
United States
Deborah
The price is HK$825
HK$2,250 total
includes taxes & fees
25 Jan - 26 Jan
Renovated 2BR Retreat / Modern Comforts Included
Interior
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Watertown
8.6 out of 10, Excellent, (10 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is HK$694
HK$954 total
includes taxes & fees
18 Jan - 19 Jan
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Interior
The Nest At Elm City Flats.

The Nest At Elm City Flats.

The Nest At Elm City Flats.
West New Haven
9.4 out of 10, Exceptional, (6 reviews)
"We had a great stay at this apartment. You do have to go up three flight of stairs but thankfully we were able to climb them. "
United States
Joan S.
The price is HK$695
HK$1,814 total
includes taxes & fees
14 Jan - 15 Jan
The Nest At Elm City Flats.
Terrace/patio
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Tunxis Hill
10.0 out of 10, Exceptional, (1 review)
"A very nice, easy, clean upper level unit. Very comfortable and easy to stay. Room for our family move and enjoy the area! "
United States
Chad L.
The price is HK$968
HK$2,462 total
includes taxes & fees
31 Jan - 1 Feb
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Fridge, microwave, oven, stovetop
One bedroom apartment in United States of America, New Haven

One bedroom apartment in United States of America, New Haven

One bedroom apartment in United States of America, New Haven
Dwight
9.4 out of 10, Exceptional, (3 reviews)
"Apartment was very clean and well supplied, host very responsive. Location is convenient to Yale and restaurants. As noted in the listing, you'll have to carry your luggage up 4 flights of stairs. There is some street noise as is typical for that part of the city. Very happy with it overall and plan to stay again."
United States
Philip S.
The price is HK$740
HK$1,590 total
includes taxes & fees
19 Jan - 20 Jan
One bedroom apartment in United States of America, New Haven
1 bedroom, iron/ironing board, WiFi, bed sheets
Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is HK$897
HK$2,263 total
includes taxes & fees
14 Jan - 15 Jan
Once the old Schools house now a newly furnished Apartment
Interior
2 Mi to Beach, Shared Yard Space: West Haven Apt!

2 Mi to Beach, Shared Yard Space: West Haven Apt!

2 Mi to Beach, Shared Yard Space: West Haven Apt!
3.0 star property
West Haven
The price is HK$1,068
HK$2,791 total
includes taxes & fees
25 Jan - 26 Jan
2 Mi to Beach, Shared Yard Space: West Haven Apt!
TV, offices
Beach Apartment in Woodmont Milford 102

Beach Apartment in Woodmont Milford 102

Beach Apartment in Woodmont Milford 102
2.0 star property
Milford
The price is HK$538
HK$2,361 total
includes taxes & fees
14 Jan - 15 Jan
Beach Apartment in Woodmont Milford 102
Fridge, microwave, oven, stovetop
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Southington
10.0 out of 10, Exceptional, (1 review)
"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."
United States
Cindy M.
The price is HK$680
HK$3,852 total
includes taxes & fees
25 Jan - 26 Jan
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Dining
Spacious 2 Bedroom apartment close to Yale Bowl

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, (69 reviews)
"The apartment was very clean and convenient. Will definitely stay there again. "
United States
Joan S.
Spacious 2 Bedroom apartment close to Yale Bowl
Interior
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Downtown Bridgeport
10.0 out of 10, Exceptional, (4 reviews)
"Nice little spot with a great host."
United States
J M.
The price is HK$959
HK$1,625 total
includes taxes & fees
20 Jan - 21 Jan
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Seymour Hotel Reviews

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

10/10 Excellent
"The staff was kind and courteous from the moment we arrived. Our room was very clean and our breakfast was good as well. We would most likely return if in the area in the future."
Cara 1-night trip
Posted 3 days ago
Holiday Inn Express Southington by IHG

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
  • Use the map to find apartments and other holiday homes in the Seymour neighbourhood you prefer
  • 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 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?

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound: This holiday home rental outside of Seymour is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 Beacon Falls Town Recreation Field and West Rock Ridge 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.