Holiday houses in Westbrook

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Top-rated holiday rentals in Westbrook

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Apartment in Chester

4.95 out of 5 average rating, 313 reviews

Chester Village 'Pied-à-terre' above art gallery

If finding a place in an ideal location w/ thoughtful design matters to you, then you've found it! Sunshine filled living room w/ high ceilings, a private bedroom in back w/ large private deck overlooking Pattaconk Brook. Our place is a gem, and set up for the comfort of our guests. Located in the heart of Chester Village, above our art gallery & boutique, and neighbor to some of the BEST restaurants, art and shopping in CT! NEW! Winter weekdays - ONE night stays are now available - message us!

13 – 20 Nov

$2,535 AUD total

Guest favourite

Home in Old Saybrook

4.98 out of 5 average rating, 48 reviews

Steps to Beach! *Cozy Cottage* Pet Friendly

Relax and enjoy the beach life in this newly renovated charmer just steps from The Saybrook Manor Assoc private beach which is only available to Saybrook Manor Assoc members. Enjoy cooking your favorite family meals in our fully stocked kitchen or venture out to some of the best restaurants on The CT Shore with a short 5-15 min drive. Free wifi for work or entertainment , private outdoor patio dining and serenity await you. You will feel at home in our little slice of heaven on The Shore.

2 – 9 Nov

$2,162 AUD total

Guest favourite

Cottage in Chester

4.98 out of 5 average rating, 229 reviews

Updated cottage "Beriozka" on Cedar Lake

Originally from Russia (hence the name “Beriozka” meaning Birch Tree) I live in Stamford CT. About 7-8 years ago I’ve discovered Chester/ Essex area and fell in love. I’ve been coming here during summer to enjoy river rides, during winter just to see snow on the ground of old towns and needless to say during fall – when all the beauty of nature unfolds. Then came an idea to have an own place here and when an opportunity came to buy this small cottage on Cedar Lake I’ve jumped on it.

13 – 20 Mar

$2,834 AUD total

Guest favourite

Home in Westbrook

5.0 out of 5 average rating, 26 reviews

Sea Salt Air Changes Everything

Sea Salt Air Changes Everything... The mood. The conversation. The momentum. When you are here you will find yourself at the crossroads of nature and civilization. Stroll to a private association beach from this restful retreat. Stretch out on the deck overlooking swaying seagrass. Sing in the outdoor shower. Go on, no one is listening. Tasteful appointments. Elegance abounds. Salt life refined with the comforts that nourish your soul. Solitude awaits you.

16 – 23 Nov

$4,371 AUD total

Guest favourite

Apartment in East Haddam

4.9 out of 5 average rating, 105 reviews

Penny Corner Airbnb

My place is located up the hill from Good Speed Opera House. The Opera House is on the same side of the river as my place. The folklore is that vacationers used to pay a penny to have their belongings transported by ox and wagon from the port at the river to this corner. A two family home built in 1884. The space is a ground level 1 bedroom apartment with private entrance. There is no TV in the unit, WIFI is available for your devices.

6 – 13 Mar

$1,264 AUD total

Guest favourite

Guest suite in Westbrook

4.98 out of 5 average rating, 40 reviews

*Newly Renovated* Private Suite - Steps to Beach!

Escape to the charming coastal town of Westbrook, CT and experience ultimate luxury & comfort in our private guest suite! Completely renovated in 2022 with modern amenities, lighting, heating/cooling, and more! After a long day exploring the town or enjoying the beach nearby, relax in the comfortable rocking chairs on the front porch, or retreat to your cozy private suite where you can rest comfortably in luxurious bedding & linens.

4 – 11 Nov

$2,514 AUD total

Guest favourite

Guest suite in Old Saybrook

5.0 out of 5 average rating, 37 reviews

Cozy Loft Getaway

The private loft is bright and airy with vaulted ceilings and all brand new furniture and appliances. The kitchen and bathroom were thoughtfully designed and sourced from our design showroom right downstairs! Minutes from local beaches and only blocks from shops and our favorite food spots in town, we hope you enjoy our beautiful and cozy loft as much as we do!

28 May – 4 June

$2,028 AUD total

Guest favourite

Apartment in Deep River

4.82 out of 5 average rating, 171 reviews

Loft apartment, deck and great water view

Great location, walk to town & only steps to the Connecticut River. Great for train aficionados- you can watch and photograph the famous Essex steam train in action.This historic factory built in 1874 has manufactured sails, metal objects and lastly Lace. Enjoy your private comfortable apartment with river views and deck.

9 – 16 Jan

$1,493 AUD total

Superhost

Home in Westbrook

4.86 out of 5 average rating, 134 reviews

Family-Friendly Cottage by The Shore

Whether you’re simply traveling to the area or planning your next vacation, you’ve found the right place. Leave your worries behind and come enjoy our freshly updated home by the shore. With a clean, comfortable and convenient spot to stay you are free to explore & relax.

13 – 20 Sept

$2,551 AUD total

Guest favourite

Loft in Essex

4.94 out of 5 average rating, 404 reviews

Unique apartment in former art gallery.

The apartment is private and in a separate wing of a converted factory complex which includes an owner occupied building and artist studio in a quiet residential neighborhood. We gladly welcome well behaved pets for an extra fee of $50.

31 May – 7 June

$2,274 AUD total

Guest favourite

Townhouse in Westbrook

4.92 out of 5 average rating, 184 reviews

Wake up with views of the ocean

Located in sleepy Westbrook, Ct and across the street from Long Island Sound, this beach house is spacious with a full kitchen, dining, and living room. A large back yard for children to play and parents to barbeque is included.

23 – 30 Aug

$5,966 AUD total

Guest favourite

Loft in Westbrook

5.0 out of 5 average rating, 59 reviews

Lovely one bedroom studio with on-site parking.

Lovely studio apartment located in a peaceful wooded area. Five mins. from I95, beaches, outlet malls, train station, restaurants and forty minutes from casinos. Great location with so much to do on the shoreline.

30 Sept – 7 Oct

$1,815 AUD total