
House vacation rentals in Westbrook
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Top-rated house rentals in Westbrook
Guests agree: these houses are highly rated for location, cleanliness, and more.

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!

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.

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

Walk to the beach at Black Point, Niantic, Ct
Black Point beach home (5th house from water) within walking distance of three beaches. Open floor plan with three levels. Ping Pong room on lower level. Living room, dining room, sitting area, and kitchen on mid level. Three bedrooms & 2 full bath on top level. WI-Fi, linens, coffee, water provided. Fenced in back yard with gas grill. Close to casinos, charter fishing, Essex steam train, Mystic Aquarium & Seaport, and Newport (1 Hr). Walk Niantic Bay Boardwalk or Old Black Point.

Connecticut Chalet: Winter Nights by the Fire
Escape to a unique & stylish home perfectly tucked away in a picturesque New England town. Indulge in the privacy & serenity of this 5 acre wooded property and peaceful pond while being minutes from an abundance of restaurants, shops & entertainment. Enjoy the natural setting from the comfort of the glass enclosed sunroom with panoramic views of the property. This 3 bed, 2 bath home maintains it’s original 1960’s charm while boasting thoughtful modern touches and intentional functionality.

“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!

Sag Harbor Wonder, 3 bedroom 2 Bath & Heated Pool
Situated on a half-acre of land, this classic shingle cottage with brand new designer interiors offers the ideal Hamptons getaway. Located in the picturesque village of Sag Harbor, less than a mile from town, bay beaches. 10 minute drive to Wolffer & ocean beaches. 3 bedrooms, 2 modern bathrooms and heated pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

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!

Harbor Heights
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).

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!

The Cozy Nook
Our Cozy Nook is a comfortable and spacious apartment with an open floor plan. Nestled in a peaceful country neighborhood makes it a relaxing get away. Nearby we have endless hiking trails, beaches, the Connecticut River and cozy villages with delicious dining, two professional theaters, galleries and one of a kind shops. The Nook offers a warm and welcoming place to stay while enjoying the surrounding area.

Family Stays, CT
Centrally Located Cozy Family Vacation Home: Just 1.2 miles from Wesleyan University, our welcoming home is an ideal choice for families, solo travelers, couples, professionals, business travelers, and almost anyone. Whether you're here to explore Middletown or the surrounding Connecticut towns, you'll have the entire property to yourself for a comfortable and enjoyable stay.
Popular amenities for Westbrook house rentals
House rentals with a pool

Hilltop House w/POOL/SPA- HOST & Co.

FREE Private Indoor Heated Pool - Mystic Home

Cozy, serene and private large Hamptons home

Cheerful East Hampton home with Pool

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)

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

Secluded Farmhouse - Studio Apartment Style Unit

Modern farmhouse w/ pool, beach, horses and winery
Weekly house rentals

Beachside Bliss w/ Game Room, Gym & Golf Green

Barnacle Bay Beach House

Beachside @ 455 Seaside

Chalker Beach House Steps to the Water

Private 1-Bdrm Apt in West Haven

Soundscape Beachfront House!

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

Coastal Getaway - walk to town and waterfront
Private house rentals

Corwin House

Duckling Crossing | Beach House on the Sand

Plant Lovers Paradise

Adorable Cottage with porch, walk to water & town

Waterfront NoFo Cottage w/ public beach access

Old Saybrook CP Beach House Walk to Water-Views

Zion's Light Beach Cottage

Money Point Beach House- Deck+Views + Beach Access
When is the best time to visit Westbrook?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$52,733 GYD | G$59,584 GYD | G$51,902 GYD | G$54,186 GYD | G$60,206 GYD | G$72,455 GYD | G$75,777 GYD | G$80,967 GYD | G$69,549 GYD | G$62,282 GYD | G$60,206 GYD | G$58,546 GYD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
Quick stats about house rentals in Westbrook

Total vacation rentals
Explore 80 vacation rentals in Westbrook

Nightly prices starting at
Westbrook vacation rentals start at G$16,609 GYD per night before taxes and fees

Verified guest reviews
Over 2,430 verified reviews to help you choose

Family-friendly vacation rentals
70 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
80 of Westbrook vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Westbrook rentals

4.9 Average rating
Westbrook stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with pools Westbrook
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- House rentals Connecticut
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- Yale University
- Foxwoods Resort Casino
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Cooper's Beach, Southampton
- Ocean Beach Park
- Sunken Meadow State Park
- Long Island Aquarium
- Mohegan Sun
- Sherwood Island State Park
- Mount Southington Ski Area
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Mystic Seaport Museum
- Sleeping Giant State Park
- East Matunuck State Beach
- Yale University Art Gallery
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