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Seymour holiday rentals

We found 131 holiday rentals — enter your dates for availability

Discover a selection of 131 holiday home rentals in Seymour that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Stayz holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at AU$ 80 per night, and holiday houses and flats & apartments are popular options for a stay in Seymour. Either way, you'll find holiday accommodation for everyone's needs.
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Find the best place to stay — Seymour

Perfect for Work Travelers

Sleeps 2 · 1 Bedroom · 1 Bathroom
AU$ 128 avg/night

Cute country cottage for getaway stay

Sleeps 3 · 1 Bedroom · 1 Bathroom
AU$ 270 avg/night
(52)

Peaceful Pinewood Retreat 1 hour from NYC, close to Yale, SHU, & FU!

Sleeps 7 · 4 Bedrooms · 2 Bathrooms
AU$ 640 avg/night
(28)

CLEAN, COMFORTABLE APT. NEAR YALE, NEW HAVEN, AND AREA COMPANIES

Sleeps 1 · 1 Bedroom · 1 Bathroom
AU$ 80 avg/night
(3)

Elegant Country Estate Guest House

Sleeps 4 · 1 Bedroom · 1 Bathroom
AU$ 266 avg/night
(44)

1ST FLR APT Your Private Resort, now FAMILY-ized

Sleeps 4 · 1 Bedroom · 1 Bathroom
AU$ 256 avg/night
(12)

Search 131 holiday rentals

Top rated rentals — Seymour
Stayed Apr 2021

Wonderful stay, quick drive from NYC

This was such a wonderful weekend trip! Pat and Gabe are great hosts. They were very responsive to our messages before and during the stay, and were super accommodating as we were traveling with our 8 month old baby and our dog. The apartment itself ...

Gary P.
Gary P.
Stayed Mar 2021

FANTASTIC house!

We had a wonderful time at The Bassett House. The property is absolutely beautiful, sparkling clean, and has every amenity you could possibly think of. Michael was helpful and friendly in his communications, and ensured we had everything we needed be...

Lindsay M.
Lindsay M.
Stayed Feb 2021

Lovely Stay

Enjoyed a quiet and peaceful getaway. The cottage was very clean, updated, and just as described. The property owner made herself available for any questions/concerns and responded quickly. Only downside was no blinds in the common area of the cottag...

Edelly P.
Edelly P.
Stayed Feb 2021

A Place to Heal and Relax

Janet (truly a superhost!) mentioned that this is a happy property--the houses and land are joyful. Indeed they are. With so many windows in the house, you feel a part of that nature. You awaken to the view of trees and sky, and in the shower, you ne...

Stephanie W.
Stephanie W.
Stayed Jan 2021

Beautiful, spacious home perfect for large family gatherings.

Perfect home for large family gathering in the CT woods. House was well kept and spacious. Kitchen and oversized dining room made a family dinner for 15 very comfortable. Host was available 24/7. We had a senior citizen on oxygen with us and they wen...

Kenneth W.
Kenneth W.
Stayed Jan 2021

Remarkable Penthouse Apt.

I greatly enjoyed my stay. Marc, the owner, is a pleasure to work with. He thought of everything and even stocked the refrigerator! The location is great for walking to get coffee and bagels in the morning or Italian food at night. Overall great expe...

Steven H.
Steven H.
Stayed Jan 2021

Superb Stay

Martha is very friendly and, equally importantly, highly responsive and helpful. A bit more detail about the house, which we plan on visiting again for certain: 1. Extremely well-organized home and the very specific labeling made everything a lot sm...

Maroun M.
Maroun M.

New York City

Stayed Dec 2020

Perfect Stay in New Haven

The property was really clean and well kept. Christopher provided a well equipped house that met all our needs. He was also extremely quick to respond and offered us beverages to consume. Will certainly recommend to any one looking to stay in the New...

Ronal G.
Ronal G.
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Destination guide

The charming city of Seymour awaits you

The beaches and surrounding scenery provide a peaceful ambience to your holiday home in Seymour. This romantic and welcoming city entices travellers with its restaurants and shopping. Yale Bowl and East Rock Park are just a couple of the must-see attractions in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities

Sightseeing in and around Seymour

Do you want to find top things to see and do in the area? Venture out of your holiday home and check out everything that makes Seymour a fun spot to go on holiday. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Yale Golf Course (6.8 mi / 11 km)
  • Great River Golf Club (7.3 mi / 11.8 km)
  • Laurel View Country Club (8 mi / 12.9 km)
  • Grassy Hill Country Club (8.2 mi / 13.3 km)
  • Sleeping Giant Golf Course (10 mi / 16.1 km)
  • Quassy Amusement Park (10.5 mi / 17 km)
Natural highlights

Exploring the natural landscape of Seymour

Whether you're looking for fun outdoor activities or just want to take in the scenery, Seymour is a great place to get out in nature. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • East Rock Park (9.9 mi / 15.9 km)
  • Osborndale State Park (2.9 mi / 4.7 km)
  • Matthies Memorial Park (3 mi / 4.9 km)
  • Beacon Falls Town Recreation Field (4.2 mi / 6.8 km)
  • West Rock Park (6.8 mi / 10.9 km)
  • Southford Falls State Park (6.8 mi / 10.9 km)
How to get there

Travelling to and around Seymour

Fly into Oxford, CT (OXC-Waterbury - Oxford), the closest airport, located 7.3 mi (11.7 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to New Haven, CT (HVN-Tweed - New Haven Regional), which is 12.8 mi (20.5 km) away.

How many holiday accommodation are available around Seymour?

Our 2021 accommodation listings offer a large selection of 131 holiday rentals around Seymour. From 40 holiday houses to 73 flats & apartments, find unique holiday homes for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Seymour is on Stayz.