Vacation rentals in Chester

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.

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.

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 suite with king bed and private entrance

Come and relax in our spacious one-bedroom basement guest suite that is comfortable and bright. It has a private entrance with off street parking. The suite has a large living area, bedroom with king bed and private bath . The location is an ideal 20 minutes from the Manchester/Boston Regional airport and 10 minutes from the Merrimack Premium Outlets as well as a wide variety of restaurants. Boston, skiing, the beach and the #1 most hiked mountain in the world are all about an hour away.

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!

Pet-Friendly 2BR| Parking+Laundry | Prime Location

Welcome to your home away from home in Manchester! This cozy, first-floor apartment offers two bedrooms, a full bath, and space to comfortably accommodate up to four guests. Enjoy the ease of driveway parking for 1 car, in-unit laundry, and no stairs—perfect for families, professionals, or anyone looking for a relaxed, accessible stay. We’re pet-friendly, so bring your furry friends! Centrally located— quick access to dining, hospitals, downtown, and more. We look forward to hosting you!

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.

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.

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

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!

Little Lake House-fishing, relaxation, waterfront

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.

Spacious Lakeside Getaway Apartment (Unit 2)

Bring the whole family to this great place with lots of room for fun 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 with a queen-sized bed pull out couch, large bedroom with king sized bed, and a fully stocked kitchen. Enjoy free shared lake access! Seasonal dock and kayak usage (mid Apr - late Oct)