
Holiday rentals in Chester
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Top-rated holiday rentals in Chester
Guests agree: these stays are highly rated for location, cleanliness and more.

Sanctum 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 large pool, hot tub, and lake access, The Sanctum 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.
4.93 out of 5 average rating, 285 reviews
Romantic A-Frame cabin in the woods
Stay at Hidden Pines Cabins. Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.
5.0 out of 5 average rating, 325 reviews
Manchester’s home away from home
Welcome Home! A spacious colonial in the very quiet east side of Manchester NH. A Short 2 min drive to Route 93 close to airport (MHT) and downtown Manchester. The first floor features formal dining, large kitchen, eat-in, half-bath plus Laundry, and a large open living room. The second floor features a spacious and bright master bed as well 2 other large bedrooms and 2nd bath.The finished basement is setup with a new 4K projector. Outside you have an appealing space with grill. Turo available.
5.0 out of 5 average rating, 143 reviews
Sunny Horse Farm Studio With Pasture Views
Our spacious studio apartment includes a fully equipped kitchen, billiards/ping pong table, 60” flatscreen TV with Roku, propane fireplace, and private patio with pergola and wood-burning firepit. We are located at the top of a 1000 foot dirt driveway, surrounded by fields and woods. Your space is in the walk-out basement of our home, and includes one queen bed as well as a queen fold-out Koala couch. There is a private entrance, with plenty of parking. Price includes Airbnb 15.5% service fee.
5.0 out of 5 average rating, 57 reviews
Residence of Manchester
Relax with the whole family at this spacious, traditional home overlooking a conservation area. Enjoy the large outdoor deck equipped year round with a propane grill. Experience the fresh air of spring, the gorgeous reds and oranges of autumn, or the novelty of winter and its holidays from a house that does them all! The Residence is just outside the hustle and bustle of the City but minutes away from Manchester Airport and Mall of NH with its array of shopping, restaurants and entertainment.
4.96 out of 5 average rating, 126 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.
4.87 out of 5 average rating, 151 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.
4.94 out of 5 average rating, 196 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.
4.99 out of 5 average rating, 164 reviews
Historical Winter Stay | Circa 1805 | Pet-Friendly
Welcome to Federal on Exeter! This iconic Epping 2 bedroom home is conveniently located close to many attractions and amenities. Federal on Exeter is just 20 minutes to UNH, and centrally located to other popular destinations like Portsmouth, Boston, and Exeter. This charming apartment sleeps 8 and is equipped with carefully curated decor, a fully stocked kitchen, a screened porch, grill, and plenty of living and dining space to relax. Pets allowed in accordance with our pet policy.
4.91 out of 5 average rating, 87 reviews
Little Lake House- Waterfront, Ice Fishing, & more
Welcome to our home away from home. This cozy lake get away just minutes over the border from Massachusetts is the perfect place to connect with friends and family. Enjoy days out on the water which is right outside your back door! Or nights at the fire pit enjoying the stars. We have wifi, tv w/ streaming services, laundry, a/c & heat, and kayaks to make your stay as comfortable and fun as possible. We're family friendly and have a crib for infant/baby.
4.96 out of 5 average rating, 208 reviews
Charming New England Farmhouse
This rustic New England Farmhouse (Recently listed as one of “The best Airbnb’s in New England” by Timeout!) has all the charm of an 18th century home, complete with all the amenities you need for your next getaway or vacation! With a sprawling yard, a newly renovated kitchen (great for gatherings), a massive deck, and 5 bedrooms. Our home has room for a fun family getaway or a relaxing retreat away from the city.
4.91 out of 5 average rating, 219 reviews
Hidden Ledge In-Law Apt
Thank you for your interest in Hidden Ledge! We are so happy to share our quiet corner of the little town of Sandown, NH. The property is surrounded by forest, including 20 undeveloped acres to the south. You may catch a glimpse of the neighbor’s two horses through the trees! The long, winding driveway leads to plenty of parking behind the home and your own private entrance to the apartment.
5.0 out of 5 average rating, 5 reviewsPopular amenities for Chester holiday rentals
Other great holiday rentals in Chester

4 Bedroom Wooded Gemstone Retreat
4.84 out of 5 average rating, 73 reviews
Harmony Cove Cottage
5.0 out of 5 average rating, 36 reviews
Relax and Enjoy
4.92 out of 5 average rating, 85 reviews
Remodeled NH Lakefront home-Sunrise & Sunset Views
5.0 out of 5 average rating, 31 reviews
The Sweet Suite - Close 2 MHT+93
4.91 out of 5 average rating, 34 reviews
Beautiful Farm Estate-Pool-HotTub-Plus Activities
4.87 out of 5 average rating, 75 reviews
Piscataquog Reservoir House - 26 Channel Ln
4.99 out of 5 average rating, 68 reviews
Cozy family friendly private apartment farm stay
4.99 out of 5 average rating, 159 reviewsDestinations to explore
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- Fenway Park
- Hampton Beach
- Ogunquit Beach
- Harvard University
- Wells Beach
- TD Garden
- Boston Seaport
- Boston Common
- Weirs Beach
- Revere Beach
- Boston University
- Boston Convention and Exhibition Center
- Long Sands Beach
- Freedom Trail
- Short Sands Beach
- New England Aquarium
- Boston College
- Northeastern University
- Canobie Lake Park
- Pats Peak Ski Area
- York Harbor Beach
- Cape Neddick Beach
- North Hampton Beach
- Harvard Square





