Holiday rentals in Chester

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chester

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

%{current} / %{total}1 / 1
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, 301 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
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, 573 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.

Top guest favourite
The exterior of the home and attached apartment is shown, featuring a light-colored facade with dark trim. A paved driveway leads to a two-car garage, surrounded by landscaping of shrubs and trees. An American flag is displayed, providing a welcoming touch.
Flat in Londonderry
4.97 out of 5 average rating, 154 reviews

The Birch Suite: Large, Cozy NH Themed Apartment

Our home and attached apartment is tucked away in a quiet neighborhood in southern NH, just minutes from major N/S highway Route 93. We are thrilled to offer our New Hampshire-themed apartment to individuals, couples and families. Each room is decorated to represent the most interesting aspects of our state: the purple lilac bathroom, the maple bedroom, the white birch living room and a large second bedroom/playroom we call "the state room" - a fun, educational room of all things New Hampshire.

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
4.79 out of 5 average rating, 266 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, 199 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.

Top guest favourite
Guest suite in Hanover Hill
4.95 out of 5 average rating, 235 reviews

Large with private entrance & a mile from downtown

This sunny, private suite with a separate entrance and driveway is convenient to everything. If you are going to a concert at the Arena, working downtown, visiting Elliot Hospital, or needing a place to stay while in the Manchester area, it is the place for you. A microwave, refrigerator, coffee pot, sitting area, and dining table make meals easy. Your full bathroom comes with soft towels and a hairdryer. The bedspread is washed between guests to ensure your stay is comfortable and clean.

Top guest favourite
The studio features a spacious bed with white linens, accented by decorative throw pillows. A vibrant piece of art adorns the wall above the bed. A modern vanity area with a sink is visible, along with natural light filtering through windows that offer views of the surrounding woods.
Guest suite in Milford
5 out of 5 average rating, 157 reviews

New England Village Luxury Studio

Kick back and relax in this stylish studio! Our house is in a quiet neighborhood of older homes surrounded by woodlands yet conveniently located downtown, a half mile from our village green (Milford Oval). A short stroll over the river will take you to cafes, restaurants, pubs with live music, post office, library, shops & useful stores such as CVS. Whatever brings you…business, skiing, hiking, antiques, a family celebration or a romantic weekend away…we are looking forward to hosting you!

Top 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, 181 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.

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.
Flat in Derry
4.75 out of 5 average rating, 404 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
A well-appointed bedroom features a comfortable queen-size bed adorned with blue and white patterned bedding. On either side, matching lamps provide soft lighting. Fresh towels are neatly arranged at the foot of the bed, while a small nightstand accommodates a remote control.
Home in Derry
4.86 out of 5 average rating, 516 reviews

Little Lakehouse, the Lookout

Cozy up during your next trip to southern New Hampshire! The Lookout, situated right next to a serene lake, boasts 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 to 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 favourite
A cozy outdoor seating area features two wooden chairs arranged around a circular stone fire pit. The space is surrounded by landscaped mulch and bordered by a winding pathway. Lush greenery and a home can be seen in the background, contributing to a serene atmosphere.
Loft in Barrington
4.96 out of 5 average rating, 558 reviews

Sunny, secluded studio loft apartment

Fully furnished studio apartment above home owners' garage with private entrance. Secluded 5.5 acre lot of land surrounded by beautiful woods. Vaulted ceilings with ladder to loft with queen bed. Big, sunny south-facing windows overlooking back yard and gardens. Homeowners are a laid-back, married gay couple, living in the main house with their 5 year old daughter. LGBTQ friendly home that welcomes kind guests of any race, religion, gender, and orientation. A minute from Route 125.

Top guest favourite
The exterior of a colonial-style house is presented, featuring a symmetrical façade with a front porch, white railing, and wide steps leading to the entrance. A well-manicured lawn and garden flank the pathway, which guides toward the door. The vibrant greenery complements the home.
Home in Haverhill
4.97 out of 5 average rating, 115 reviews

Charming 4-Bedroom Colonial

Welcome to this charming colonial nestled within the tranquil suburban Bradford section of Haverhill, Massachusetts. This inviting four-bedroom, 2.5-bath residence offers a serene retreat for those seeking a comfortable and spacious accommodation. This home is perfect for you and your family looking to enjoy your time spent in the awesome private outdoor space near the fire-pit or indoors enjoying a wonderful home cook meal at the dining table gathered around by your love ones.

Popular amenities for Chester holiday rentals