House holiday rentals in Westbrook

4.97 out of 5 average rating, 224 reviews

A balcony view captures a serene beachfront scene at sunset, with gentle waves lapping at the sandy shore. A detailed metal chair is positioned on the deck, providing a quiet spot to enjoy the tranquil waters and cloudy sky.

Home in Niantic

Beachfront Paradise

Beautiful beachfront home available weekly in season third week of June through Labor Day) and nightly (2 night min.) off season. Step out the door and into the sand. Sit on the porch and watch sailboat races from Niantic Bay Yacht Club just steps away. Close to downtown Niantic with restaurants, shops, etc. 18 miles from Mohegan Sun Casino. Attractions within 1/2 hour: Beautiful Mystic, CT, several vineyards, Harkness State Park, Eugene O'Neill Theatre, U.S. Coast Guard Academy, golf courses.

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.

4.97 out of 5 average rating, 143 reviews

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

A newly remodeled home is set amidst a lush green lawn, featuring a spacious front porch with blue Adirondack chairs. The exterior is characterized by a blend of gray siding and a welcoming entryway, surrounded by a well-maintained garden and a wooden sign.

4.96 out of 5 average rating, 28 reviews

Remodeled cozy home near beach

.4 mile walk to Beach/Westbrook Elks Club, this newly remodeled home is perfect for a couple looking to relax and enjoy what the CT Shoreline has to offer. Close to restaurants and shopping, this house boasts a spacious queen bedroom, walk in shower, large kitchen, living room, dining room, sitting area, 2 gas fireplaces, & laundry room. Enjoy the private outdoor deck with dining table, Adirondack chairs, porch swing and hot tub. Cook outside on the Weber grill or take a ride on bikes provided.

4.93 out of 5 average rating, 343 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.

4.98 out of 5 average rating, 57 reviews

Secret Seaside Stone Cottage

Create unforgettable memories at the Secret Stone Cottage, a retreat in the scenic coastal town of Westbrook, Connecticut. Offering 2,200 SF of refined living space and outdoor living amenities along the serene Patchogue River, this unique property is the ultimate destination for family reunions, shared vacations, and milestone celebrations. With sweeping waterfront views and sophisticated amenities, it also serves as an enchanting, intimate venue for unforgettable weddings and special events.

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.

4.8 out of 5 average rating, 146 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 wooden dock stretches over the calm waters, supported by several sturdy posts featuring black caps. The sky above is clear with soft clouds, enhancing the serene coastal atmosphere.

4.92 out of 5 average rating, 104 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.

A historic New England home features a classic white exterior with multiple windows. Surrounding greenery includes mature trees and a well-maintained lawn. The side of the house provides a glimpse of a separate structure, enhancing the spacious outdoor area.

4.97 out of 5 average rating, 220 reviews

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.

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, 185 reviews

Amazing 2BR Riverfront Gem

Unwind at this happy getaway on the river. Extremely comfortable house with amazing views in a peaceful neighborhood. 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, music, and lots more.

A two-story waterfront home is set against a serene evening sky, featuring a spacious front lawn. Large windows invite natural light, while a balcony provides an upper-level retreat. A stone patio with seating is visible, enhancing outdoor relaxation options.

4.94 out of 5 average rating, 35 reviews

Red Bird Waterfront Home. Dock available extra!

Looking for a stylish and spacious place to stay for your next group trip? Look no further than this waterfront home, perfect for families looking to relax and create lasting memories by the ocean. Interested in hosting an event? Ask us! This beautiful home offers stunning views of the water and plenty of space for your family to enjoy. Whether you're looking to spend your days lounging on the beach, exploring the nearby attractions, or simply relaxing with your loved ones.

The inviting entrance of the cottage is shown, featuring a front porch and path bordered by lush greenery. Vibrant flowers add color to the landscape, while a warm glow emanates from the entryway, highlighted by the soft evening sky.

4.98 out of 5 average rating, 80 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.

4.93 out of 5 average rating, 142 reviews

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON

INSTANT BOOK: Aug 2026 - Jan 2027 = All Open Availability SUMMER 2026: Aug + Sept Steps away from CT Shoreline in back of beach house! Amazing Views - Waterfront Outdoor Deck w/ Seating (2nd week May - until Nov 6th) *certain holidays/summer excluded in booking minimums *discounts applied to nightly rate only *we can not combine multiple discounts, yet highest % will apply *if available, also apply 10% non-refundable booking option

Popular amenities for Westbrook house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.92 out of 5 average rating, 323 reviews

The large two-tiered deck is illuminated with soft lighting, creating a cozy atmosphere. A staircase leads to the upper level, where seating and decor are visible. An above-ground pool is situated beside the deck, surrounded by greenery and evening skies.

Home in Montville

Casino Wine Down House w/Pool, Game Room, Big Deck

4.99 out of 5 average rating, 127 reviews

The living area features two rattan chairs facing a coffee table, surrounded by vibrant wall art. A cozy sofa and plants add life to the space. Natural light streams through large windows, creating a bright and inviting atmosphere.

Home in Montauk

3 BR/Pool. Walk to Beach & Town!

4.97 out of 5 average rating, 217 reviews

A serene outdoor area showcases a saltwater pool with a spa, surrounded by well-maintained landscaping featuring vibrant yellow flowers. Lush green fields extend into the distance, framed by a clear sky with scattered clouds.

Home in North Fork

Private Oasis W/Stunning Vinyard and Pool Views

4.91 out of 5 average rating, 126 reviews

A private outdoor area features a spacious swimming pool with a connected spa, surrounded by greenery. Two decorative lion statues flank the pool entrance. Lounge chairs and a gazebo provide additional relaxation options under a sunny sky dotted with clouds.

Home in Columbia

Breathtaking home with unforgettable views & pool!

4.83 out of 5 average rating, 136 reviews

An outdoor area features a rectangular pool surrounded by a wooden deck. Lounge chairs are positioned along the pool's edge, and a shaded seating area is located nearby under an umbrella. Lush trees provide privacy and a natural backdrop.

Home in Springs

East Hampton Oasis - Pool and Hot Tub

4.91 out of 5 average rating, 246 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

4.96 out of 5 average rating, 206 reviews

A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.

Home in North Fork

Secluded Farmhouse - Studio Apartment Style Unit

4.93 out of 5 average rating, 134 reviews

A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.

Home in Mattituck

Modern farmhouse w/ pool, beach, horses and winery

Weekly house rentals

4.86 out of 5 average rating, 59 reviews

Duckling Crossing | Beach House on the Sand

A collage showcases the various entertainment and relaxation areas. The top left features a game room with arcade machines and a dartboard. The top right highlights a manicured putting green. The bottom left displays the exterior of the home with outdoor seating, while the bottom right depicts a home gym with workout equipment against a bright orange wall.

4.97 out of 5 average rating, 30 reviews

Beachside Bliss w/ Game Room, Gym & Golf Green

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.

4.59 out of 5 average rating, 34 reviews

Adorable Cottage with porch, walk to water & town

5 out of 5 average rating, 12 reviews

Historic Coastal Home • Marsh Views • Pet-Friendly

The image presents a serene beach scene, featuring a sandy pathway leading to a calm water body. A safety barrier is visible in the water, marking designated swimming areas. Lush green grass borders the beach, enhancing the tranquil coastal environment.

4.89 out of 5 average rating, 91 reviews

Zion's Light Beach Cottage

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.

4.64 out of 5 average rating, 95 reviews

Money Point Beach House- Deck+Views + Beach Access

4.76 out of 5 average rating, 34 reviews

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

4.95 out of 5 average rating, 86 reviews

Peaceful 4BR Cape w/ Sunroom | Near Beach

Private house rentals

4.83 out of 5 average rating, 65 reviews

An aerial view of a spacious home with a light-colored exterior is displayed, surrounded by scenic natural landscapes. Large windows enhance the modern design, and the Connecticut River is visible in the background, reflecting the clear blue sky.

Home in Old Lyme

Stunning house on CT river !

4.9 out of 5 average rating, 58 reviews

A charming two-story house is set on a green lawn, featuring white siding and dark green shutters. Gravel pathways lead to the entrance, and a small shed is visible to the side. Mature trees provide shade, enhancing the peaceful outdoor setting.

Home in Madison

Cozy beach cottage close to everthing

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, 39 reviews

Soundscape Beachfront House!

4.97 out of 5 average rating, 97 reviews

A white two-story house is featured, with black-shuttered windows and a decorative front porch lantern. An American flag flutters at the front, and a neatly maintained fence surrounds the lawn. A tree without leaves is visible in the background on a clear day.

Home in Essex

Ideal Historic Home in Essex Village

5 out of 5 average rating, 27 reviews

A bright living room features large windows that overlook a serene view of the pond. Comfortable gray sofas and two navy blue chairs with yellow accents are arranged around a glass coffee table on a patterned area rug. A stone fireplace adds a cozy touch to the space.

Home in Essex

Water View Mid Century Home in Essex CT, 4 Kayaks

An American flag is displayed prominently in the foreground, with the sun setting over the water in the background. The sky is painted with soft hues as the sun begins to dip beneath the horizon, illuminating the shoreline and creating a serene coastal scene.

5 out of 5 average rating, 16 reviews

Waterfront Oasis 4Bdr/2b

A charming cottage sits elevated on wooden stilts, framed by sandy beach. A set of white stairs leads up to a spacious deck with railings. Nearby, beach chairs are positioned on the sand, and a striped umbrella provides shade.

4.89 out of 5 average rating, 9 reviews

The Viola Beach Cottage