A calm lake surrounded by autumn-colored trees and a clear blue sky.

Ridgefield Holiday Rentals

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Our top choices for Ridgefield holiday rentals

1. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
10.0 out of 10, Exceptional, (1 review)
"The place is super comfortable and has a great outdoor area for chatting; I would definitely like to come back and stay longer."
United States
Yasmin G.
The price is NZ$328
includes taxes & fees
12 Oct - 13 Oct
Welcome to Sweet Abby Rose!

2. Renovated Retreat with Heated Pool

Renovated Retreat with Heated Pool
Redding
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful house, very clean, spacious and a great host!!!"
United States
Alejandro A.
The price is NZ$1,163
includes taxes & fees
12 Oct - 13 Oct
Renovated Retreat with Heated Pool

3. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Bethel
The price is NZ$234
includes taxes & fees
12 Oct - 13 Oct
1 King Bed | Non-Smoking

4. Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
9.6 out of 10, Exceptional, (9 reviews)
"lovely porch and backyard."
United States
Kaia W.
The price is NZ$1,907
includes taxes & fees
4 Nov - 5 Nov
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

5. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (114 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is NZ$472
includes taxes & fees
12 Oct - 13 Oct
DUNE Fairfield Beach

6. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is NZ$596
includes taxes & fees
13 Oct - 14 Oct
Guesthouse at Norwalk Inn

7. 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
9.6 out of 10, Exceptional, (14 reviews)
"Perfect option for a quick visit, Would stay again!"
United States
Destiny
The price is NZ$345
includes taxes & fees
9 Nov - 10 Nov
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

8. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (190 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is NZ$310
includes taxes & fees
12 Oct - 13 Oct
Stamford Suites

9. 2 Queen Beds | Non-Smoking

2 Queen Beds | Non-Smoking
Bethel
The price is NZ$244
includes taxes & fees
12 Oct - 13 Oct
2 Queen Beds | Non-Smoking

10. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Bethel
The price is NZ$224
includes taxes & fees
12 Oct - 13 Oct
1 Queen Bed | Non-Smoking

11. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (59 reviews)
"Definitely clean - good place for an overnight stay."
United States
Kimberly
The price is NZ$271
includes taxes & fees
12 Oct - 13 Oct
Business or Weekend escape

12. Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!

Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
Downtown Stamford
10.0 out of 10, Exceptional, (3 reviews)
"Had a lovely stay. Close to the train station and close to things in Stamford. Lovely space and owner was super helpful!"
United States
Marisa C.
The price is NZ$476
includes taxes & fees
12 Oct - 13 Oct
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!

13. 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.
The price is NZ$216
includes taxes & fees
18 Oct - 19 Oct
Cozy One Bedroom Apartment Centrally Located in Southbury

14. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (45 reviews)
"Nice stay"
United States
Christopher J.
The price is NZ$621
includes taxes & fees
12 Oct - 13 Oct
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

15. Modern Apartment with Private Entrance

Modern Apartment with Private Entrance
Historic District
The price is NZ$527
includes taxes & fees
12 Oct - 13 Oct
Modern Apartment with Private Entrance

16. Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
New Fairfield
8.6 out of 10, Excellent, (36 reviews)
"Very serene location, the host was very responsive and helpful."
United States
Stephen L.
The price is NZ$580
includes taxes & fees
18 Oct - 19 Oct
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

17. The Perch in the Purchase -- Cozy, unique, and private

The Perch in the Purchase -- Cozy, unique, and private
Southbury
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is NZ$410
includes taxes & fees
25 Oct - 26 Oct
The Perch in the Purchase -- Cozy, unique, and private

18. Centric property close to all the great things in the city

Centric property close to all the great things in the city
Brooklawn - St. Vincent
6.6 out of 10, (17 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is NZ$470
includes taxes & fees
12 Oct - 13 Oct
Centric property close to all the great things in the city

19. Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"loved walking the city. pizza was good."
United States
michelle b.
The price is NZ$546
includes taxes & fees
18 Oct - 19 Oct
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
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 Ridgefield Hotel Reviews

Find out more about Ridgefield

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Ridgefield holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Ridgefield. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Ridgefield. Seeing all the best attractions is bound to make you fall in love with Ridgefield. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Ridgefield short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Ridgefield?

Yes, there are holiday rentals in Ridgefield close to Ridgefield Playhouse, or you can select a more secluded option if you're looking for a relaxing stay. Ridgefield is known for its spas and monuments. Make sure you have time to check out the live music and golf courses during your trip.

What are some of the best holiday rentals that Ridgefield has to offer?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This holiday home rental outside of Ridgefield offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 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.

How many holiday rentals are there in Ridgefield?

Expedia has 4 holiday rentals for your stay in Ridgefield.

What’s there to see and do in Ridgefield?

Enjoy the outdoors at Mamanasco Beach and Weir Farm National Historic Site, or simply take in cultural attractions like Ridgefield Playhouse and Prospector Theater. While here, Twixt Hills Beach and Wooster Mountain State Park are other places worth a visit.

What’s a holiday rental in Ridgefield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Ridgefield. Holiday rentals feature amenities like kitchens and laundry facilities so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for family trips.