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Holiday rentals in Cobbetts Pond

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Top-rated holiday rentals in Cobbetts Pond

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

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Top guest favourite
A spacious home sits on a manicured lot, featuring a well-kept garden and an expansive driveway. The two-story structure boasts large windows and a welcoming entrance, with outdoor lighting enhancing its features during twilight. The attached garages are visible on the right.
Guest suite in Windham
4.99 out of 5 average rating, 319 reviews

Sunny, private and peaceful apartment!

Our home sit in a private and peaceful setting. It is perfect for the business travelers looking for a place to relax at the end of the day or anyone looking for a quiet place. Close to Castleton Banquet and Conference Center, Searles Castle, Canobie Lake Park, walking & biking trails, shopping and restaurant. Centrally located between Boston, beaches and mountain and lake region. Only 16 miles from Manchester Boston Regional Airport, 36 miles from downtown Boston, 3.5 miles from Interstate 93.

Guest favourite
An open living area is presented, featuring a dark leather sofa facing a circular dining table with wooden chairs. A well-equipped kitchen, complete with modern appliances, is visible in the background. Natural light enters through large windows, illuminating the wood flooring.
Flat in Windham
4.86 out of 5 average rating, 256 reviews

The Estate Escape with Hottub

The apartment is new with high-end finishes, but there is still a storage container outside in the front of the house. (See pictures.) Cozy up during your next trip to southern New Hampshire! The Estate Escape is a perfect place for a peaceful escape with its own hot tub. The Estate Escape is minutes away from Canobie Lake Park, Castleton, and La Belle Winery. It is a short drive to Manchester Airport, and about an hour to Boston, the NH Seacoast, NH Lakes Region and the White mountains.

Top guest favourite
A modern kitchen is presented with white cabinets and stainless steel appliances, including a refrigerator and oven. Granite countertops provide ample workspace, with a sink beneath a window. Natural light fills the area, enhancing the open and inviting atmosphere.
Flat in Windham
4.89 out of 5 average rating, 373 reviews

The Cozy Corner Apartment

Cozy up during your next trip to the southern New Hampshire area! The Cozy Corner is a combination of style and comfort in so many ways from the double windows and sliding glass doors that flood the space with light to the airy and peaceful design that makes it feel like home. The Cozy Corner is a short drive to Canobie Lake Park and Manchester Airport, 45 minutes to Boston and NH Seacoast, close to Lakes Region, White mountains, and great skiing spots. 10 minutes from major shopping centers!

Guest favourite
The dining area features a wooden table surrounded by four high-backed chairs. A large piece of artwork is displayed on the wall, and a potted plant adds a touch of greenery. The open kitchen is visible in the background, equipped with modern appliances.
Flat in Derry
4.87 out of 5 average rating, 146 reviews

3 Bedroom Apartment in Downtown Derry

Cozy up during your next trip to southern NH! Built in 1910, this apartment has been completely renovated. Meadowview is a combination of elegance and comfort from the walls of windows that flood the space with light and scenic conservation/golf course views to the spacious backyard that is perfect for a peaceful escape. It is 5 minutes from i-93 and a short drive to Canobie Lake Park, Manchester Airport, and about an hour to Boston, the NH Seacoast, NH Lakes Region and the White mountains.

Guest favourite
A serene view of the lake is framed by two bright blue chairs and a small white table topped with a pot of yellow flowers. Lush greenery surrounds the water, with residential homes visible in the distance.
Home in Salem
4.94 out of 5 average rating, 194 reviews

Quaint Little New Hampshire Lake House Getaway!

Imagine the peace and quiet of looking out a wall of glass seeing the tranquility of the lake while knowing 10 minutes away is shopping, restaurants entertainment and just about anything you could ask for to meet your needs. 10 minutes from the highway, 35 minutes from Boston, 35 minutes from the ocean and 1 1/2 hours from the mountains. We are a central point to anything you’re looking for. Newly renovated lake house with all the up to date amenities. Come and enjoy a night or week.

Top guest favourite
A bright yellow two-family home is positioned amidst greenery, featuring a welcoming entry with a red door. A small flowering tree adds a splash of color in front, while a large deck is visible in the background, perfect for outdoor gatherings.
Home in Chelmsford
5.0 out of 5 average rating, 259 reviews

Newly renovated, spacious, clean, 3 bedroom home.

Whether traveling for business or pleasure, this ideally located, pet-friendly home in North Chelmsford, Massachusetts, is accessible to major highways and commuter rails. The home is close to major hospitals, universities, and concert venues. The area is rich in America’s history and is surrounded by historical sites to visit all within minutes. The beautiful, light, airy living space boasts all the comforts of home. Our goal is to give you the best travel experience possible.

Top guest favourite
The charming waterfront cottage is surrounded by dense greenery, reflecting beautifully in the calm water. A spacious porch extends from the structure, offering an inviting space to enjoy the serene lakeside setting.
Cottage in Windham
5.0 out of 5 average rating, 28 reviews

Lakefront! Johnson Point Cottages-“Morningside”

Canoe, fish and swim from the private beach and swimming area and then enjoy a BBQ on the patio. Take in the sunrise on the deck while sipping your morning coffee in this charming NH waterfront cottage. Boasting hard wood floors, ceiling beams, and a bonus room upstairs with a second floor balcony, this cottage fills all the dots for a refreshing getaway. Week not available? Check out our two other listings! To learn more visit us on social media @johnsonpointcottages

Guest favourite
A cozy living area features a sectional sofa adorned with decorative pillows and a coffee table at its center. Natural light pours in through two windows, complemented by sheer curtains. A decorative wheel and framed wall art enhance the space, along with potted plants.
Cottage in Windham
4.74 out of 5 average rating, 100 reviews

Lake Cottage in Windham

Welcome to our lake cottage, the perfect family getaway! Just a short walk to a private beach on Cobbets Pond, enjoy sunbathing and swimming. For more adventure, Canobie Lake Park, Castaway Island, and Searles Castle are nearby. For even more adventure, Boston and Salem, MA are both under one hour away! Whether seeking relaxation or fun, our cottage offers the best of both worlds, plus local restaurants, shops, and friendly faces. Your ultimate escape awaits!

Superhost
An outdoor seating area features four blue chairs arranged around a fire pit, with cushions providing comfort. A red umbrella shades a nearby table for four, while a propane grill sits ready for use. A charming cottage is visible in the background, surrounded by trees.
Cabin in Windham
4.88 out of 5 average rating, 104 reviews

Big Fish, Little Lake - Fire Pit & Pvt Beach

Please read Other Details to Note @DiamondHomeCollection on Insta Come Fish & Kayak here! Our area is full of life and peace. Wake up to the loons early in the morning and go to bed listening to the owls. Watch the turkeys or fox cross the yard. Our homes are from the 1920's, we keep them alive and for the souls who love old homes. 45 minutes to the ski destinations ocean, lakes region, and hiking. Not waterfront, we own shares of waterfront.

Top guest favourite
A contemporary cabin retreat is nestled among tall trees, softly illuminated by warm outdoor lights. A wooden deck with steps leads to a welcoming entrance. A separate sauna structure is visible, surrounded by snow-covered ground, providing a serene atmosphere in a tranquil forest setting.
Home in South Berwick
5.0 out of 5 average rating, 146 reviews

Romantic Mirror cabin in the woods

Stay at Hidden Pines Cabins. The Mirror cabin is Maines only 3 sided floor to ceiling mirrored glass cabin. Unwind in the hot tub while looking up at the sky full of stars. Take a sauna while surrounded by nature all around. Located in the majestic forest of mount Agamenticus, the extensive trail system is off of our road. Short drive to the Ogunquit/York beaches, Outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

Top guest favourite
A private backyard oasis is surrounded by lush greenery and blooming flowers. A swimming pool is featured in the foreground, reflecting blue skies. Outdoor seating areas are visible, providing space for relaxation and enjoyment.
Home in North Andover
4.95 out of 5 average rating, 184 reviews

Nana-tucket Inn

Charming historic town, home of Brooks School and Phillips Academy, 30 minutes to Boston and Seacoast. Families will enjoy our children’s park and town park, just a short walk from property. Enjoy pastural views while relaxing poolside (availability May 1 - Oct 1)in a quiet & private backyard setting. Hot tub is also open May 1 til Nov 1. Seven minutes to commuter rail for those who desire traveling into Boston, no hassle!

Top guest favourite
An open living space features a comfortable sofa, a coffee table, and a twin bed with a white bedspread. Large windows allow natural light to fill the room. A dining table is visible in the adjacent area, enhancing the inviting layout.
Guest house in Windham
4.88 out of 5 average rating, 98 reviews

Private Guest House

Very convenient location. Close to 93 N/S. Minutes from Canobie Lake Park, Castleton Banquet Conference Center, and Searles Castle, Comman Man and Lobster Tail Restaurants, 5 minute walk to Windham Town Beach, 20 Minutes to Manchester Airport, and 40 minutes to Boston Logan Airport.

Popular amenities for Cobbetts Pond holiday rentals