Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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Guest favorite

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.

Top guest favorite

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!

Guest favorite

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.

Apartment 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 favorite

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 favorite

A cozy living room features a plush sectional sofa arranged around a stylish coffee table. A large smart TV is positioned against a white brick wall, and artwork depicting serene landscapes adorns the adjacent wall, contributing to a relaxed ambiance.

Home in Derry

4.83 out of 5 average rating, 30 reviews

Idyllic Small-Town Stay (2 Bed)

Discover the charm of Derry, NH in this quaint 2-bedroom home! On the peaceful outskirts of a small town, 3 min from I-93 with easy access to Boston (45 min) and Manchester (15 min). Cozy living space with modern amenities, fully equipped kitchen, and dedicated workspace. Shared backyard patio with a grill & fire pit. Perfect for families and friends seeking a relaxing retreat with small-town vibes and convenience. Explore local treasures like Canobie Lake, vineyards, and Robert Frost Farm!

Top guest favorite

Guesthouse in Alton

4.98 out of 5 average rating, 442 reviews

The Vineyard Penthouse - Beautiful Inside & Out

Wake up to rows of sun-kissed grapevines and unwind in a serene, vineyard-view retreat. This open-concept suite featured a plush king bed, abundant natural light and inviting modern décor. Sip wine at sunset, cook in the well-equipped kitchen and savor the tranquility of your private space. Although there are other guest on the property you will have this space to call your own and enjoy. ~ 5 min from Lake Winnipesukee, 20 min to Wolfeboro, 20 min to Gunstock and 25 min to Bank of Pavilion

Top guest favorite

A light-filled living area features large windows draped with sheer curtains, allowing ample natural light. A spacious sectional sofa is centered in the room, accompanied by a glass dining table. A dedicated workspace with a stylish chair is positioned near the windows.

Apartment in Manchester

4.97 out of 5 average rating, 72 reviews

The Dreamcatcher ~ Luxury New Apt, Prime North End

Wake up in a stunningly artistic, spacious studio in the heart of Manchester’s prime North End! Just minutes from downtown’s best restaurants & attractions, this safe, quiet & private apartment is in a high-end building with luxury finishes. Designer-renovated and brand new—from interior & systems to the roof. Featuring: - Full, well-equipped kitchen 🍽️ - Dedicated workspace 💻 - Convenient parking spot 🚗 - Bright, airy space filled with natural light ☀️ Full list of amenities below 👇

Top guest favorite

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.

Guesthouse 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.

Superhost

A cozy living area features a light-colored sofa adorned with plush throw pillows. Natural light floods in through large windows, illuminating the space. A tabletop and decorative plant are visible in the background, adding a touch of warmth to the inviting ambiance.

Apartment in Derry

4.76 out of 5 average rating, 397 reviews

Downtown Derry, Studio Apartment

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

Superhost

The master bedroom features a spacious bed adorned with textured bedding and decorative throw pillows. A macramé wall hanging adds visual interest above the bed, and a softly lit lamp provides gentle illumination, creating a serene environment.

Apartment in Manchester

4.91 out of 5 average rating, 33 reviews

Cozy Central Downtown 2BD Unit Close to 93 & Elm

Enjoy this stylish space at this centrally located apartment right in downtown Manchester, designed for you and your family to relax, and enjoy what New Hampshire has to offer. We designed this space to accommodate your everyday needs as well as please the eye. Located on a very busy/noisy street. ✓ 2 Mins to downtown Elm Street ✓ 3 Mins to Interstate 93 ✓ 5 Mins to the Elliott Hospital ✓ Tons of things to do/eat close-by ✓ Free on-site parking ✓ Easily Accessible ✓ Private Entrance

Guest favorite

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.

Guesthouse 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!

Guest favorite

A modern bedroom features a queen-size bed with a light blue and white coral-patterned quilt. Two matching pillows sit at the head of the bed. A nightstand is positioned beside the bed, and natural light enters through a small window above.

Guesthouse in Manchester

4.93 out of 5 average rating, 40 reviews

Urban Oasis: Modern Studio in Manchester’s Heart

Welcome to your private urban oasis! This brand new, modern studio is perfectly tailored for solo travelers or couples seeking a blend of comfort and convenience in Manchester, NH. Ideal for: 1-2 guests Bed: Queen size with memory foam mattress Kitchen: Fully-equipped with coffee maker and kitchenware Bathroom: Private, with all essentials Entertainment: 50-inch TV with Netflix Comfort: Heat and AC for your ideal temperature Access: Private entrance for your convenience