Holiday houses in Southeastern Connecticut Planning Region

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Top-rated holiday rentals in Southeastern Connecticut Planning Region

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

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Top Guest favourite

A serene landscape is presented, featuring expansive green fields under a softly glowing sunrise. Two rustic buildings are visible: a barn with classic doors and a white cottage, both surrounded by lush trees and open space, reflecting the peaceful countryside setting.

Guesthouse in North Stonington

4.99 out of 5 average rating, 244 reviews

"Mystic Country" Farm Stay at 100 Acre Wood

Let us welcome you to 100 Acre Wood, a historic farm and working cattle ranch. Owl's House is a private and stylish guest house nestled within the trees and garden and offers 180° views. Our farm store is stocked with our own TX Longhorn beef and pasture-raised chicken and eggs, plus curated with local products. Enjoy pastoral farm life and our private forest trails, or get out and play in the area's abundance of fine dining, wineries, seasonal attractions, outdoor activities, and entertainment.

Top Guest favourite

A cozy bedroom features a dark upholstered headboard with an arrangement of plush pillows. Soft lighting is provided by a bedside lamp, creating a serene ambiance. Above the bed, three art pieces depict a sun motif, adding warmth to the neutral wall color.

Home in Norwich

4.95 out of 5 average rating, 151 reviews

Cozy Condo in Norwich- Minutes from Mohegan Sun

This Stylish first floor Suite is perfectly located at the Villas at the Norwich Inn, steps from the main clubhouse with the heated (seasonal) saltwater swimming pool, Jacuzzi, exercise room, saunas and shower. Short walk to The Spa at Norwich Inn. Easily walk to the Norwich Golf Course and indoor ice rink. Take a short drive to beaches such as Rocky Neck, Mohegan Sun for entertainment, restaurants and shopping (only 1 mile away) or Foxwoods for zip lining, bowling, go Karts and Tanger Outlets.

Guest favourite

A serene view of the Poquetanuck Bay is captured at dawn, showcasing a calm water surface reflecting pastel hues of pink and purple. Surrounding trees frame the scene, while homes on the opposite shore are silhouetted against the soft morning light.

Home in Preston

4.95 out of 5 average rating, 776 reviews

Entire House Magical Waterfront Getaway

4 MINUTES TO MOHEGAN SUN! Yet quiet and secluded! Waterfront home! Come relax in this 3 bedrooms 2 baths well appointed home with breathtaking view of the Poquetanuck Bay! Enjoying the absolutely gorgeous view from the balcony or porch! Or simply relax, sit around, enjoy each other’s company! Smart TV grants you easy access to thousands of streaming apps! 25 minutes to Ocean Beach, Mystic seaport, Mystic aquariums, Submarine and Library Museum in Groton! 15 minutes away from Foxwood casino!

Top Guest favourite

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

4.93 out of 5 average rating, 336 reviews

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.

Guest favourite

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

4.91 out of 5 average rating, 244 reviews

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

Welcome to the Lucky Lounge! Minutes away from Mohegan Sun, Foxwoods, Mystic, Naval Submarine Base, USGC College, CT College, and numerous beaches. We have all you need to enjoy your time inside and outside during your stay! - Hot tub - Private pool - Fire pit - Pool table - NFL Blitz 4 player arcade game - Air hockey - Foosball - Giant connect four - Corn hole - Darts - Karaoke - Smart TV - Board games - Ultra comfy beds - BBQ - Kid friendly - Super fast WiFi - Stocked kitchen

Top Guest favourite

A cozy houseboat is seen floating on the water, featuring a welcoming porch with two light blue chairs. The reflection of the boat and surrounding trees is visible in the calm river, highlighting the serene atmosphere of the setting.

Boat in Old Lyme

5 out of 5 average rating, 102 reviews

Sunny Daze

This dreamy houseboat rests gently at a family-owned marina, where time seems to slow and nature leans in close. Surrounded by peaceful river views, tall grasses, and birdsong, it’s a floating haven for those seeking calm and creativity. Whether you’re sipping coffee on the deck at sunrise or watching the moon ripple across the water, this riverside retreat invites you to drift, dream, and just be. Enjoy a fire or jump on a paddle board or kayak f or an adventure down the river it has it all!

Top Guest favourite

A comfortable living area features a gray sectional sofa with a chaise lounge, positioned across from a minimalist entertainment unit. Natural light filters through sliding glass doors that lead to a patio. A dining area is visible in the background, accompanied by bar stools.

Condo in Norwich

4.98 out of 5 average rating, 357 reviews

Top Rated Villa located near Mohegan Sun & Mystic

Located on the Norwich Inn and Spa property, this Villa is a true one bedroom unit with access to two clubhouses (9am-10pm) which include a sauna, gym, hot tub, and saltwater pool access (seasonal). It is also located a few miles away from both Mohegan Sun Casino and Foxwoods Resort and Casino with many amazing restaurants to chose from in the area. If you are a fan of golf, we are located right on the back 9 of the Norwich Golf course! Lake of Isles golf course is also about 15 minutes away.

Top Guest favourite

The exterior view features a small wooden cabin surrounded by vibrant green trees. A stone path leads to a seating area, comprising four metal chairs and a table. Inside, the cozy octagonal space is lit by natural light filtering through several windows, showcasing a full-sized bed adorned with a colorful patterned quilt.

Tiny home in Norwich

4.99 out of 5 average rating, 949 reviews

Water Forest Retreat -Octagon

Water Forest retreat is a very private 122ft.² electrified and heated cedar octagon next to a brook on 56 acres of forest with a pond, waterfall, marsh and hiking trails. Cozy up in this quiet comfortable space while listening to Goldmine brook while you sleep. Fire pit, heated outhouse with composting toilet, outdoor dining area, brook, pond and trail head are just steps away. We also have a TREE HOUSE and HIKER’S HAVEN house by the brook. Please click on our profile picture to read more.

Top Guest favourite

Condo in Norwich

4.99 out of 5 average rating, 244 reviews

Peaceful Oasis steps from Mohegan Sun

Feel at home at our contemporary yet cozy villa. A private and quiet space in the heart of the area's local attractions (walkable to Mohegan Sun/short drive to Foxwoods). Perfect for a fun-filled weekend or a simple and quiet getaway. Enjoy the scenic views of the surrounding golf course or indulge at the on-site renowned spa. Other noteworthy amenities include a year round opened clubhouse, sauna, and hot tub as well as two beautiful seasonally opened pools. This unit comfortably sleeps 4.

Top Guest favourite

The exterior of the cottage is characterized by a charming stone chimney and a vibrant green door. The white siding contrasts with lush greenery, while a small seating area features two colorful chairs on the well-maintained lawn. A stone pathway leads toward the entrance.

Cottage in East Haddam

5 out of 5 average rating, 105 reviews

Historic Hearthstone Cottage

Built in 1800 and thoughtfully renovated in 2024, this two-story guest cottage can be the retreat of your dreams. Surrounded by thousands of acres of nature preserve, short walks to scenic vistas, a raging waterfall and countless hiking trails, few places are as peaceful as Hearthstone. Whether you’re looking for a private oasis or romantic getaway, are a parent sharing the beauty of nature, or an artist looking for inspiration, this historic cottage is for you.

Top Guest favourite

A bright blue kayak is positioned at the edge of a calm cove, with tranquil water reflecting soft pastel hues of twilight. Lush greenery lines the shore, and a wooded landscape extends into the distance, creating a serene setting for kayaking.

Home in Montville

4.87 out of 5 average rating, 102 reviews

Cozy Cape on the Cove

Our two-bedroom cape on the cove is a paradise for any birdwatcher, fisherman, or kayak enthusiast. We are located near any destination you may want (i.e. casinos), yet far enough off the beaten path to enjoy some peace and quiet. Listen to the birds and crickets by the firepit or take out our rentable kayaks for a morning paddle. Dogs welcome too! Pet fee is $50 per stay. Maximum 2 dogs. Maximum of 3 guests. Any unauthorized guest will be charged at $50/each.

Top Guest favourite

A living area features a comfortable sofa and two armchairs, arranged around a rustic coffee table. A fireplace is set into a stone mantel, and a large television is mounted on the wall. Sliding doors lead to a private balcony, allowing natural light to fill the space.

Condo in Norwich

4.98 out of 5 average rating, 193 reviews

The Vacay Villa

The Vacay Villa, minutes away from Mohegan Sun, Foxwoods and The Spa at Norwich Inn, offers so many amenities you won’t have to leave the grounds. Private balcony, fireplace, two outdoor pools opened seasonally, year-round access to hot tub and saunas, small workout room, laundry facilities, allow for a one-of-a-kind stay at an incredibly affordable price. Why spend hundreds to stay at the area casinos and hotels when you can stay in your own private villa?