House holiday rentals in Westbrook

4.98 out of 5 average rating, 130 reviews

A charming cottage is depicted with a shingle exterior, a welcoming front porch, and a chimney. The grassy landscape is flanked by flowering shrubs, and a path leads to the entrance. A red barn is visible in the background, enhancing the rural setting.

Home in Waterford

Niantic River Beach Cottage | Waterviews

Kick back and relax in this quiet, stylish New England beach cottage with water views, a private neighborhood beach, an outdoor shower, and a sunny patio for coffee or evening wine. Just minutes from downtown Niantic, you’ll find beaches, cafés, bakeries, ice-cream stands, seafood, boutiques, boat launches, trails, outdoor concerts, and more—all within a short drive or bike ride. Perfect for a romantic getaway, a family weekend, or some quiet coastal downtime. See why guests love staying here!

5 out of 5 average rating, 159 reviews

Home in North Haven

Luxury Stay in Expansive Historical Home

The Bassett House, originally built in 1802, this large historic farmhouse was elegantly remolded in 2018. North Haven, CT is centrally located and just minutes from Yale, Quinnipiac, UNH, and SCSU as well as shopping, the best restaurants, hiking trails state parks and beaches, and many local attractions including various vineyards. If you’re planning a business trip or a gathering for family or friends, then our home can provide you with an exceptional level of comfort during your time in CT!

4.96 out of 5 average rating, 133 reviews

A two-story home features a light-colored exterior with traditional shutters and a welcoming front porch. The yard is neatly landscaped with greenery and flowers. A wooden deck is visible at the back, providing an inviting outdoor space.

Home in Saybrook Manor

Year Round Beach House in Old Saybrook, CT.- Pets

Our Beautiful Home is Located in Saybrook Manor Association and only a short walk to the beach . We have 4 Bedrooms that can accomadate 8 people,pull out couch,2 bathrooms, a Dining Room,Kitchen, and Spacious Living room.Our Yard is fenced in for your privacy & pets.Our home comes with many ammenities such as movies,games,kayaks, Clamming &Crabbing tools,Bikes,Floats & Beach Chairs.We have a beautiful backyard to enjoy games,barbecue or just to relax & unwind.Enjoy our beautiful & quaint beach

4.93 out of 5 average rating, 270 reviews

A tranquil lake scene is captured at sunrise, featuring a wooden dock extending into the water. Soft pink and orange hues reflect on the lake's surface, complementing the surrounding greenery. Two Adirondack chairs sit near a fire pit, inviting relaxation by the scenic view.

Home in East Haddam

Romantic Getaway at The Lake!

Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

A serene outdoor space is presented, featuring two black adirondack chairs positioned on a well-maintained lawn. Colorful flower pots are placed on either side of a small table, with lush greenery surrounding the area and a tranquil lake visible in the background.

4.79 out of 5 average rating, 136 reviews

The Dragon Fly Garden

The phrase "nestled in nature” is the best way to describe the dragonfly's den. Sitting on the trail head to over 1,000 acres of the Cocaponsette State Forest across from Messerschmidt pond and just three miles from the winding salt water marsh water way you won't find a better mix of activities. Golf & boating are just moments away. Mountain biking & Trail running off the property. This country cottage boasts lake views, wildlife and wandering trails to loose yourself within. 1GB internet

A charming stone exterior is visible, featuring a private entrance with a sliding glass door. The path is made of stone, surrounded by a well-maintained lawn. In the background, sitting areas and greenery are discernible, enhancing a serene outdoor experience.

4.92 out of 5 average rating, 170 reviews

Amazing 2BR Riverfront Gem

Unwind at this happy getaway with an amazing river view, peaceful neighborhood, and in the heart of fall foliage and holiday scenes. The well-equipped kitchen overlooking the river is a pleasure for any cook. You will love to see our fairy-lit lawn, wishing well, chimenea, and charming décor. Only minutes to beaches, groceries, coffee shops, hiking trails and amazing CT scenery at every turn! Other favorites include Chamard Vineyard, Shopping Outlets, fantastic Restaurants, and lots more.

4.99 out of 5 average rating, 134 reviews

A cozy living area features a comfortable gray sofa and an armchair positioned around a circular wooden coffee table. A flat-screen television is mounted above a brick fireplace. Natural light enters through multiple windows, highlighting the inviting space.

Home in Hebron

Welcome to The Avery!

Welcome to The Avery at Amston Lake! Great three-bedroom lake cottage situated in a peaceful lake community. Great place to slow down and relax. Lay out in the sun on the beach, enjoy a fire in the backyard, and even spend some time playing games in the cozy sun room! We are located near numerous vineyards, a brewery, the Connecticut Airline Trail, and great local restaurants! Guests have access to the grill, fire pit area, two kayaks located at the kayak launch, and two main beaches.

4.98 out of 5 average rating, 210 reviews

An open-concept kitchen and living space features modern appliances and a wood-topped island with seating for three. Light cabinets and blue walls create a bright environment, while a hallway visible in the background leads to the entrance of the cottage.

Home in Branford

“The Lighthouse” A Beach Cottage by the Sea!

Relax at this unique and tranquil getaway. Long Island Sound to the left, hiking trails to the right. Come kick your feet up at this quiet dead-end road. Enjoy all the modern amenities in this gem of a cottage community. Restaurants and nightlife are just a quick stroll away. Avoid roadside hotels and take a vacation for a night, week, or longer! Check in anytime and at your convenience!No keys to lose or to return! This property provides secure, keyless entry with an August Smart Lock!

4.97 out of 5 average rating, 209 reviews

Home

Waterside Beach Retreat

Beautiful New England period home steps from the beach on the Long Island Sound. Recently renovated from top to bottom with new kitchen and bathrooms, hardwood floors throughout. Idyllic location on quaint & quiet street. Hide away and relax or discover the many local attractions - water sports, fishing, winery, antique stores, scenic walks, premium outlet shopping are all on your doorstep. Ideally located off the I-95 halfway between NYC & Boston, both of which are a train ride away.

4.99 out of 5 average rating, 143 reviews

An open-concept living space features light-colored wood flooring and a cozy seating area with a white couch and wooden coffee table. A small dining table is positioned nearby, while a stylish staircase leads to an upper level. A television is mounted on the wall, adding to the modern atmosphere.

Home in Haddam

Cozy Comforts!

Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

4.94 out of 5 average rating, 380 reviews

A bright living room features a comfortable gray sofa against a neutral wall, complemented by a light-colored rug with geometric patterns. A wooden coffee table sits in front, with a lounge chair nearby. Natural light enters through multiple windows, creating a spacious feel.

Home in North Fork

The Sandpiper

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

A living area features a comfortable sectional sofa adorned with decorative pillows. Two light blue armchairs are positioned beside a small table with a patterned top, while a television stand and a floor lamp complete the inviting space. Sunlight is visible through a window.

4.92 out of 5 average rating, 106 reviews

Best of both worlds!

Great location- 1 mile to the beach, 1/2 mile to shops and restaurants, and less than a 1/4 mile to a park! The house is set back from the road with a good size driveway. The inside is newly renovated and we are working to finish the yard area for the summer! The house has WiFi, large yard, and a great front porch that gets a ton of sun. We’ve made great memories there over the years and are now looking to share it with others!

Popular amenities for house rentals in Westbrook

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.86 out of 5 average rating, 126 reviews

Aerial view of a spacious home surrounded by lush greenery, showcasing a large pool with a deck. Solar panels are visible on the roof. The property is set in a serene wooded area, providing a sense of privacy and tranquility.

Home in Stonington

Homestead Near Mystic, Casinos & Beaches

4.92 out of 5 average rating, 297 reviews

Home in Montville

Casino Wine Down House with Winter Igloo

4.98 out of 5 average rating, 45 reviews

Home in North Fork

Corwin House

4.91 out of 5 average rating, 199 reviews

The exterior of a Cape Cod style beach house is captured at sunset, showcasing a spacious upper balcony with an umbrella and illuminated railings. The warm hues of the sky enhance the inviting atmosphere of the home, while surrounding trees add to the serene setting.

Home in New London

Sunset Oasis 1 @ Ocean Beach: $1Mil View 6 Queen

4.98 out of 5 average rating, 122 reviews

Home in Stonington

FREE Private Indoor Heated Pool - Mystic Home

4.9 out of 5 average rating, 204 reviews

The exterior of a single-story home is presented, featuring a manicured lawn and a symmetrical facade. Solar panels are installed on the roof. Large windows are visible, providing natural light to the interior. A path leads to the front door, flanked by neatly trimmed shrubs.

Home in Montville

Hot Tub~Pool~GameRoom~FirePit~BBQ~King Bed~Casinos

4.9 out of 5 average rating, 121 reviews

A swim spa with dual zones is shown, featuring illuminated blue and red lights. The adjacent outdoor area includes a large screen displaying a sports event. Steam rises from the hot tub, creating a relaxing ambiance in the evening setting.

Home in Hamden

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton

4.97 out of 5 average rating, 153 reviews

An expansive aerial view reveals a private pool surrounded by lush green grass and trees. A small pond is visible nearby, with vibrant foliage framing the scene. Open fields stretch into the distance, highlighting the rural setting on the property.

Home in Windham

mid century ranch style house on farmland

Weekly house rentals

4.97 out of 5 average rating, 69 reviews

A spacious beachfront property is showcased, featuring a well-maintained lawn and a patio area with outdoor seating. The ocean is visible in the background, providing serene water views. The home is characterized by its coastal architecture and nearby neighboring structures.

Home in Branford

Adorable Beach House on LI Sound

A cozy living area features a brown sofa with decorative pillows and a neutral-toned ottoman. A round green pouf adds a pop of color. Natural light enters through large windows adorned with sheer curtains. A small dining table is situated nearby with two chairs, enhancing the inviting atmosphere.

5 out of 5 average rating, 9 reviews

Plant Lovers Paradise

A beachfront view captures a private sandy beach with an outdoor umbrella and seating area. The chic living room features large windows overlooking the sea, showcasing light neutral tones and plush seating. A glimpse of a cozy bedroom reveals inviting furnishings and bright accents.

4.85 out of 5 average rating, 53 reviews

Duckling Crossing | Beach House on the Sand

5 out of 5 average rating, 25 reviews

Old Saybrook CP Beach House Walk to Water-Views

4.88 out of 5 average rating, 26 reviews

A sunlit living area features large triangular windows that offer expansive views of the ocean. Comfortable seating includes a beige sectional sofa and a patterned armchair, complemented by a small table. Natural light floods the space, creating a bright and inviting atmosphere.

Home in Saybrook Manor

White Bird Beachfront. Dock available extra.

A sunny wraparound deck is featured with multiple seating options, including four Adirondack chairs and a dining table sheltered by a large umbrella. The surrounding views include coastal greenery and distant houses, highlighted against a clear blue sky.

4.61 out of 5 average rating, 87 reviews

Money Point Beach House- Deck+Views + Beach Access

4.85 out of 5 average rating, 20 reviews

Cozy Beach Home Mid NYC-Bos/Comfy Getaway all year

5 out of 5 average rating, 39 reviews

A comfortable living area features a gray sofa positioned around a low coffee table. A television rests on a media console against the wall, with natural light streaming through two windows that overlook greenery outside.

Home in Higganum

The Doll House

Private house rentals

A charming duplex features a light blue exterior with white trim and a welcoming front porch. Two Adirondack chairs are positioned on the porch, inviting relaxation. Windows enhance natural light, while neatly trimmed shrubs add greenery to the inviting facade.

4.75 out of 5 average rating, 32 reviews

Adorable Cottage with porch, walk to water & town

4.9 out of 5 average rating, 39 reviews

The exterior of a modern cottage is presented with a black wood facade and multiple windows. A front porch is seen, partially enclosed with slatted wood. Lush green grass and shrubbery frame the entrance, creating a welcoming approach to the home.

Home in North Fork

Waterfront NoFo Cottage w/ public beach access

A comfortable living area features two plush brown sofas positioned around a rectangular coffee table. Natural light filters in through multiple windows, highlighting a soft area rug beneath. Decorative accents include a nautical-themed wall piece and two neatly arranged throw pillows.

4.9 out of 5 average rating, 40 reviews

Newly renovated CT shoreline home next to Marinas

A modern kitchen is highlighted by white cabinetry and marble countertops, featuring high-end stainless-steel appliances. An adjacent dining area with a wooden table and chairs is visible in the background, providing a spacious and inviting layout.

4.95 out of 5 average rating, 60 reviews

Water Views and Walk to Beach

A bright living area features large windows that overlook the ocean, allowing natural light to fill the space. The room is furnished with a blue sofa, two armchairs, and a coffee table. A small plant adds a touch of greenery, and a dining area is visible in the background.

5 out of 5 average rating, 37 reviews

Soundscape Beachfront House!

A light-filled living area features a spacious sectional sofa draped with a cozy throw. A wooden coffee table sits nearby, with a guitar resting against the wall. A dining table with chairs is visible, complemented by large windows allowing natural light.

5 out of 5 average rating, 18 reviews

Private Beaches-3 Bedroom, king bed-beach walk

4.87 out of 5 average rating, 89 reviews

A modern design villa is situated on a lush hillside, surrounded by greenery. The structure features clean lines and large windows, blending with the natural landscape. In the background, the Connecticut River glimmers under the sunlight, adding to the serene atmosphere.

Home in Deep River

Modern Starship: Winter River Views Await

A dining table is set for four on a wooden deck, with plates and wine glasses arranged on a glass top. A bottle of wine is present. In the background, a vast yard with trees and clear blue skies creates a serene atmosphere.