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Westport Holiday Rentals

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Check prices for these dates

Tonight
1 Aug - 2 Aug
Tomorrow
2 Aug - 3 Aug
This weekend
1 Aug - 3 Aug
Next weekend
8 Aug - 10 Aug

Holiday Rentals in Westport

Sweet Studio w/ Lounge & Pool Table
Relax in this stylish living room with a large flat-screen TV, comfortable sofa, and a round coffee table.

Sweet Studio w/ Lounge & Pool Table

10.0 out of 10, Exceptional, (3)
"This was our first time getting a VRBO while coming up for a family July 4th party. Everything was great. The space was clean and very comfortable and looked just like the pictures. It was only 5 minutes from our family’s house and very easy to find and in a nice neighborhood. The host was great and very easy to communicate with. "
The price is HK$1,256
HK$2,357 total
includes taxes & fees
3 Aug - 4 Aug
Sweet Studio w/ Lounge & Pool Table
Stamford Suites
Welcome to our reception area, featuring a polished reception desk, pendant light fixture, and patterned wallpaper with a geometric design.

Stamford Suites

4.0 star property
5.6 out of 10, (48)
"It was great relaxing stay"
The price is HK$1,180
HK$1,357 total
includes taxes & fees
3 Aug - 4 Aug
Stamford Suites
DUNE Fairfield Beach
Enjoy a serene beach experience with a tranquil atmosphere, perfect for relaxation or contemplation.

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (62)
"Incredible staff, friendly, helpful. "
DUNE Fairfield Beach
Guesthouse at Norwalk Inn
Welcome to our hotel, where a grand entrance sets the tone for a memorable stay.

Guesthouse at Norwalk Inn

3.5 star property
8.4 out of 10, Very good, (39)
"it was amazing will stay again food was good comfort was great "
The price is HK$1,884
HK$2,166 total
includes taxes & fees
19 Aug - 20 Aug
Guesthouse at Norwalk Inn
Business or Weekend escape
Enjoy a refreshing swim under the stars at our pool, surrounded by a spacious deck.

Business or Weekend escape

9.2 out of 10, Wonderful, (42)
"Very nice owner with great communication. "
The price is HK$667
HK$1,150 total
includes taxes & fees
4 Aug - 5 Aug
Business or Weekend escape
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access
Enjoy the ocean view from this room, featuring a sofa, chair, and small table.

Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

10.0 out of 10, Exceptional, (5)
The price is HK$2,975
HK$5,455 total
includes taxes & fees
11 Aug - 12 Aug
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins
Kitchen features a refrigerator, microwave, stove, and sink, with a rug and window.

(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

9.0 out of 10, Wonderful, (7)
"This property is well maintained. Some amenities available that made our stay more enjoyable. My only issue was the amount of noise you could hear throughout the night.but once you're asleep it doesn't matter. "
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Relax in this serene bedroom with a large arched window, a cozy seating area, and a minimalist design featuring a white bed.

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

10.0 out of 10, Exceptional, (1)
"Such a cute vibey apartment and the host was so nice and easy to talk to--would love to stay here again!"
The price is HK$1,099
HK$1,829 total
includes taxes & fees
4 Aug - 5 Aug
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Waterfront Beautiful Fun Beach Cottage Sunsets Inspiring Peaceful 1hr NYC Wow
Relax on the pier with lounge chairs and enjoy the serene natural surroundings.

Waterfront Beautiful Fun Beach Cottage Sunsets Inspiring Peaceful 1hr NYC Wow

9.0 out of 10, Wonderful, (7)
"Very comfortable space & accomodating host! Fantastic views of Northport Harbour and steps away from the water's edge! Would return and strongly recommend."
Waterfront Beautiful Fun Beach Cottage Sunsets Inspiring Peaceful 1hr NYC Wow
Modern House in Black Rock
Enjoy cooking in this well-equipped kitchen with a stainless steel sink, coffee maker, and toaster.

Modern House in Black Rock

2.0 star property
9.0 out of 10, Wonderful, (6)
"Very easy stay and great location convenient to Fairfield University . Plenty of options to walk to for coffee or meals. Had everything we needed. Clean, well equipped. Great communication with owners. "
Modern House in Black Rock
Luxury Apartments by Hyatus at The Asher
Relax in a stylish living room with a plush sofa, dark fireplace, and large window offering a view of the outdoors.

Luxury Apartments by Hyatus at The Asher

4.5 star property
10.0 out of 10, Exceptional, (16)
"The covered parking was really helpful on a cold day."
Luxury Apartments by Hyatus at The Asher
1856 Trading House close to water
Relax in this serene outdoor space with a dining table, wicker sofa, and lush greenery.

1856 Trading House close to water

9.4 out of 10, Exceptional, (17)
"Close to port Jefferson!"
1856 Trading House close to water
Charming Colonial for Events and Getaways! – Perfect for Family Retreat!
Smart TV, stereo

Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

10.0 out of 10, Exceptional, (1)
"This property is absolutely beautiful. Extremely clean. The host was very attentive to my questions before and after check in. The host checked on my family during our stay. The yard, the porches, and the entire interior are so cozy and comfortable. The check in and check out processes were smooth. The neighborhood is quiet. I am already looking forward to going back! Definitely recommend the Beechmont House"
The price is HK$5,652
HK$10,852 total
includes taxes & fees
4 Aug - 5 Aug
Charming Colonial for Events and Getaways! – Perfect for Family Retreat!
42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!
Relax in this stylish living room with a high ceiling, leather sofa, and comfortable armchair.

42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!

8.6 out of 10, Excellent, (7)
"I rented this place because of the location and convenience to the many things we enjoy about Milford CT. The master bedroom is top-notch as well as the living space downstairs. We hoped to use the outdoor fire place make smores, but due to a medical emergency our trip was cut short. Regardless, we enjoyed our stay at 42 Wood Ave. Thank you, Tiffany, for supplying an awesome rental."
42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!
My favorite place!
Relax by the pool surrounded by lush greenery and a comfortable patio area.

My favorite place!

2.0 star property
2.0 out of 10, (1)
My favorite place!
Renovated 2BR Retreat / Modern Comforts Included
Cozy retreat with a bed, bedside tables, and a comfortable chair.

Renovated 2BR Retreat / Modern Comforts Included

10.0 out of 10, Exceptional, (1)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
The price is HK$1,365
HK$2,982 total
includes taxes & fees
27 Aug - 28 Aug
Renovated 2BR Retreat / Modern Comforts Included
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Property grounds

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

9.0 out of 10, Wonderful, (7)
"Perfect place to rest. Excellent service! "
The price is HK$1,170
HK$2,303 total
includes taxes & fees
1 Sept - 2 Sept
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
My little place Cozy Open concept for quiet time.
Enjoy cooking in this well-equipped kitchen with a stainless steel refrigerator, sink, and ample cabinetry.

My little place Cozy Open concept for quiet time.

8.0 out of 10, Very good, (2)
"Great, clean property that was easy to access and very convenient to downtown Bridgeport. Perfect place to clean up and sleep. Very welcoming space."
The price is HK$1,166
HK$3,854 total
includes taxes & fees
7 Aug - 8 Aug
My little place Cozy Open concept for quiet time.
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Compact kitchen with a coffee maker and dining area with a round table and two chairs.

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

2.0 star property
10.0 out of 10, Exceptional, (5)
"Honestly i do not know where to start, everything was perfect. My friend and i needed a place to stay while celebrating a baby shower and this rental was not only the perfect location but it was a great price as well. The place was very clean, very roomy, had all the amenities we needed, and the host were very kind and attentive. This place checked all our boxes and we would absolutely stay here again next time we visit the Island. I highly recommend this rental to others!"
The price is HK$1,286
HK$1,783 total
includes taxes & fees
4 Aug - 5 Aug
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Spacious One Bedroom suite
Relax in this stylish living space with a sofa, dining area, and fully equipped kitchen.

Spacious One Bedroom suite

8.0 out of 10, Very good, (5)
"Nice stay enjoyed it "
Spacious One Bedroom suite
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 Westport Hotel Reviews

Hyatt Regency Greenwich

Hyatt Regency Greenwich

10/10 Excellent
"Very beautiful greenery area where you can have a drink or breakfast Pool was nice too And bedrooms very calm and comfortable "
ELISE 1-night trip
Posted 2 days ago
Hyatt Regency Greenwich

Frequently asked questions

Can I find holiday rentals in Westport?

Yes, there are holiday rentals in Westport close to Earthplace Museum, or you can select a more secluded option if you're looking for a relaxing stay. Westport is known for its football games and waterfront. Make sure you have time to check out the entertainment choices and theatres during your trip.

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

Business or Weekend escape: This holiday home rental outside of Westport is equipped with a BBQ, air conditioning and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a microwave and a coffee maker.

How many holiday rentals will I find in Westport?

Expedia has 57 holiday rentals for your stay in Westport.

What’s there to see and do in Westport?

Family-friendly attractions include Earthplace Museum and Rolnick Observatory, whereas Old Mill Beach and Compo Beach are a couple of great spots to enjoy the outdoors. Levitt Pavilion and Westport Country Playhouse are other places to visit while you're in town.

What’s a holiday rental in Westport like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Westport. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for small groups.