Holiday rentals in Chester

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Top-rated holiday rentals in Chester

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Guest favourite
A welcoming sitting area features two comfortable chairs beside a small round table. Natural light floods through large windows, showcasing views of the serene lake. A television is mounted above a decorative fireplace, creating an inviting space for relaxation.
Home in Derry
4.92 out of 5 average rating, 506 reviews

Little Lake House, the Bungalow

Cozy up during your next trip to southern New Hampshire! The Little Lake house, situated right next to a serene lake, boasted luxury and spectacular water views. It's a perfect place for a peaceful escape or chance to experience the wide variety of seasonal New England activities from swimming and leaf peeping to ice fishing. The Little Lake house is a short drive to Canobie Lake Park and Manchester Airport, and about an hour to Boston, the NH Seacoast, NH Lakes Region and the White mountains.

Guest favourite
A modern kitchen area features stainless steel appliances, including a refrigerator and a gas stove. Open shelving displays decorative items. A dining table and chairs are situated near the room's entrance, while a doorway leads to a bathroom in the distance.
Flat in Derry
4.95 out of 5 average rating, 77 reviews

Gorgeous Lakefront Suite Apartment (Unit 3)

Get away to a lakefront retreat in beautiful southern NH! Enjoy our 1 bedroom unit that is part of a gorgeous 3 family waterfront home. This suite comes complete with a thoughtfully decorated living room, a stocked kitchen, and furnished with a queen-sized bed and an air mattress upon request. Enjoy free shared lake access! It is 8 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.

Top guest favourite
A blue two-story house is surrounded by lush greenery, providing a serene backdrop. The front features large windows, a staircase leading to the entrance, and a spacious driveway with ample parking. Attached garage doors are visible on the right side.
Home in Hampstead
5 out of 5 average rating, 18 reviews

Lakeview Ste./Wineries/Golf/Fall Attractions/KgBd

Escape to your private cozy suite—perfect for a romantic getaway, solo retreat, or a peaceful work trip. Nestled in the heart of Southern NH, this haven blends comfort with nature. Unwind on a plush King-sized mattress while the soothing sounds of loons lull you to sleep. Start your day with a cup of coffee or a quick meal, then explore nearby beaches or scenic spots. Whether you're relaxing or adventuring, this suite offers the perfect balance of convenience and tranquility. Your escape awaits!

Superhost
The exterior of The Word Barn is illuminated against a twilight sky, showcasing its distinct architectural features. Warm lights line the entrance, and large windows reveal a welcoming interior. Surrounding greenery adds to the tranquil ambiance of the private setting.
Barn in Exeter
4.87 out of 5 average rating, 549 reviews

The Word Barn, Exeter, NH

Charming open apartment with a loft bedroom. Hardwood floors, barn beams, butcher block counter, full galley kitchen, private bath, vaulted ceilings - as part of the renovated original Raynes Farm Barn. This apartment is clean, private and isolated, with self check-in and plenty of outside space to enjoy. Located five minutes from downtown Exeter (w/plenty of take-out/delivery options) in an idyllic country setting, neighboring 100+ acre conservation land and a large network of wooded trails.

Guest favourite
The exterior of a two-story building showcases a traditional design with white siding and dark blue shutters. A welcoming entrance is highlighted by a covered front porch and a set of stairs. Surrounding greenery adds to the inviting atmosphere.
Flat in Amesbury
4.78 out of 5 average rating, 259 reviews

Lovely Downtown Oasis ~ Hospitals/Colleges/Beaches

Unwind in the modern 1BR 1Bath apt in the heart of downtown Amesbury, just a stone's throw away from tasty local restaurants and attractions. This charming oasis is perfect for leisure guests looking to explore nearby beaches and towns while also being close to hospitals and colleges, catering to traveling nurses and professionals. ✔ Comfortable King Bedroom ✔ Cozy Living Room ✔ Fully Equipped Kitchen ✔ Smart TV ✔ Workspace ✔ Washer/Dryer ✔ High-Speed Wi-Fi ✔ Free Parking Learn more below!

Guest favourite
The living area is characterized by a light and spacious design, featuring a large gray couch with decorative pillows, a white coffee table, and a cozy accent chair. Sunlight filters through the windows, illuminating the hardwood flooring and creating a warm ambiance.
Home in Derry
4.88 out of 5 average rating, 172 reviews

Haven by the Lake

Looking for a place to bring the family, or a get-a-away with friends? This is it! From the light and airy design that makes it feel like home to the hot tub, loft room, and lake access, The Haven by the Lake has everything you need for a great stay. It is a short 100 yard walk from the lake and a quick drive to Canobie Lake Park and Manchester Airport, 45 minutes to Boston or the NH Seacoast, close to the Lakes Region, White mountains, and great skiing spots as well as the famous NH Outlets.

Guest favourite
A mid-century modern living space features a vibrant orange sectional sofa adorned with colorful throw pillows. A round wooden coffee table sits on a soft area rug. Natural light fills the room, highlighting the geometric patterned wallpaper and a workspace with a chair and desk in the background.
Flat in Manchester
5 out of 5 average rating, 35 reviews

Bohemian Retreat ~ 1 BR + Flex Room, New, Central

Step into mid-century modern charm at this vibrant yet serene getaway in Manchester’s North End! Featuring a stylish bedroom with a luxury queen bed and a versatile flex room — a bright space with blackout blinds that can serve as an office, lounge, or extra sleeping area for one to two people. Perfect for families or remote workers, this thoughtfully designed retreat is minutes from downtown. Enjoy a fully stocked kitchen, elegant furnishings, workspace, free parking at your door, and more!

Top guest favourite
Apartment in Hampton Beach
4.97 out of 5 average rating, 302 reviews

Seacoast Getaway

Seacoast, NH’s popularity is well-earned, with museums, the finest restaurants, spas and shopping that blend perfectly with the Seacoast landscape. From our beautiful beaches and coastline combined with plentiful outdoor recreation, including fishing and whale watching, kite flying and more with Portsmouth, Rye, Exeter and Kittery Maine, all a short ride our beachfront condo has something for all. After a day of outdoor activity and exploring, come retire and rest in our place with a view.

Top guest favourite
An open concept living area features modern furnishings, including a sofa with yellow and neutral accents. Large windows allow natural light to illuminate the space, which leads to a well-equipped kitchen and dining area in the background, enhancing the overall spacious feel.
Flat in Derry
4.93 out of 5 average rating, 275 reviews

Downtown Derry, A Modern 2-bedroom apt.

Cozy up during your next trip to southern NH! Built in 1910, the home has been completely renovated. The Riesling 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.

Top guest favourite
The spacious living area features high ceilings and natural light streaming through large windows. A comfortable sectional couch is arranged around a wooden coffee table, with two accent chairs positioned nearby. A television is mounted on the wall, contributing to the cozy atmosphere.
Guest house in Kingston
4.99 out of 5 average rating, 118 reviews

Accessory Apt on Wooded Property

Forget your worries in this spacious and serene space. Guest House/Over Garage Apartment tucked away on 6 acres. Centrally locataed in the seacoast region of New Hampshire. Close to mountains, beaches, hiking trails, lakes, & more. 15 minutes to Exeter, 30 minutes to North Hampton/Hampton Beach, 35 minutes to Southern Maine and Portsmouth, NH, 40 minutes to Manchester Boston Regional Airport, and 1 hour to Downtown Boston yet still tucked away in your own private retreat in the woods.

Guest favourite
A cozy bedroom features a wooden bed frame with a layered blanket on a spacious bed. A light streams through a window adorned with soft curtains, illuminating the room. A leather chair sits in the corner, adding to the welcoming atmosphere.
Guest house in Londonderry
4.93 out of 5 average rating, 27 reviews

The Sweet Suite - Close 2 MHT+93

Come and stay at the Sweet Suite, a hidden gem in Londonderry, NH perfect for a weekend getaway or a traveling worker. This apartment features a sleep number bed for restful comfortable nights as well as a full eat in kitchen and living room area. Perfectly situated just 5 minutes from 93 and 15 minutes from MHT airport (We checked!). This property is well suited for commuters or for those looking to explore the great natural wonders NH has to offer. Families also welcome!

Top guest favourite
A serene lakeside view is presented, featuring a wooden dock extending over the water. Lush green trees line the shore, with a flower garden in the foreground. A small decorative figure sitting near the water adds charm to the landscape, enhancing the peaceful atmosphere.
Cabin in Nottingham
4.99 out of 5 average rating, 185 reviews

Rustic Log Cabin on Pawtuckaway Lake

Our Cabin is located on Pawtuckaway Lake in Nottingham, NH where there is year round enjoyment! This is an older cabin built in 1970, with rounded logs and lots of warmth and charm. There is a beach area for swimming, patio for hanging out enjoying the views with a firepit as well as a dock for sunbathing and fishing. There is a public boat launch on the lake if you want to bring your own boat. Close to Pawtuckaway state park for hiking and mountain biking.

Popular amenities for Chester holiday rentals