Villa Bay - Vacation Rentals in Chester

Linden Cottage - comfort, connection, convenience From US $393
         

10.0 (38 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Private Pet Friendly Single Family Home From US $168
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Ash Street Inn From US $260
         

New
Bed & Breakfast
  • Parking
  • Bedding/Linens
  • Wellness Facilities
Enchanting, romantic and fun river getawayn From US $342
         

Home away from home-7 mins from Downtown From US $350
         

10.0 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Private Waterfront Home From US $604
         

10.0 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in Chester

Over 270+ Luxury Places to Stay in or Near Chester
Charming 1825 Farmhouse Near Boston & Canobie Lake From US $1,859
         

9.8 (21 Reviews)
House
  • Air Conditioner
  • Parking
  • Security/Safety
Charming 2-Story Home Near Boston, Tuscan Village From US $1,384
         

North End Family From US $1,123
         

6.0 (1 Review)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
North End Relaxing Family From US $1,095
         

9.6 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Triple Family Unit Combined From US $1,071
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Family Oasis From US $735
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • TV
Calm Chaos Family Unit From US $640
         

10.0 (6 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Top-Rated Vacation Rentals with a Pool in Chester

Over 38+ Top-Rated Vacation Rentals with a Pool in or Near Chester
Exquisite 2 Bedroom apartment - Manchester NH From US $94
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • Balcony/Terrace
Residence Inn by Marriott Manchester Downtown From US $148
         

|
9.4 (520 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
The Daffodil 1743 Getaway Apartment From US $205
         

9.4 (50 Reviews)
Other
  • Air Conditioner
  • Parking
  • Pool
Residence Inn by Marriott Manchester Downtown From US $184
         

|
9.1 (195 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
DoubleTree by Hilton Manchester Downtown From US $146
         

|
9.0 (1104 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Fairfield Inn & Suites by Marriott Hooksett From US $113
         

9.0 (755 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
SpringHill Suites Manchester-Boston Regional Airport From US $116
         

Hilton Garden Inn Manchester Downtown From US $125
         

|
8.8 (1003 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Chester

Over 91+ Pet-Friendly Vacation Rentals in or Near Chester
The Sweet Suite - just minutes from MHT and 93 From US $146
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Peek-a-Boo Lake Views and Yard Windham Home From US $410
         

|
10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • Accessibility
Red Roof Inn Salem From US $97
         

6.8 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious Pawtuckaway Getaway From US $437
         

10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • TV
Cozy downtown Manchester 1-bedroom apartment From US $218
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Cozy Salem Studio Near Tuscan Village & Boston From US $244
         

9.8 (19 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Maplewood Retreat Pet-Friendly *NH Location* From US $241
         

9.8 (10 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Whispering Pines Pet-Friendly *NH Location* From US $235
         

9.6 (20 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Chester on PetFriendly.io

Large Vacation Homes & Villas in Chester

Over 19+ Large Vacation Homes & Villas in or Near Chester
North End Retreat From US $612
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Econo Lodge Manchester From US $351
         

|
6.3 (342 Reviews)
Cabin
  • Parking
  • Pet Friendly
  • Security/Safety
North End Family Oasis From US $548
         

9.8 (22 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Lakefront Retreat w/Kayaks, Grill, Fire Pit! From US $367
         

Peek-a-Boo Lake Views & Yard: Windham Home From US $315
         

8.4 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
5BR Luxe Lakehouse: Theater, Gym, Spa, Bar, Garage From US $612
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Wheelchair Accessible Vacation Homes in Chester

Over 35+ Wheelchair Accessible Vacation Homes in or Near Chester
Hampton Inn Manchester Downtown From US $144
         

|
8.5 (578 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Tru by Hilton Manchester Downtown From US $104
         

9.2 (1021 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Lakeside Wooded Retreat on Kingston Lake From US $226
         

10.0 (68 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Tru By Hilton Manchester Downtown From US $185
         

|
8.5 (560 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Four Points by Sheraton Bedford Manchester Airport From US $98
         

|
9.2 (223 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Relaxing Wooded Retreat with Hot Tub From US $239
         

4.9 (10 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • TV
Hilton Garden Inn Manchester Downtown From US $156
         

|
8.4 (151 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Chester Varoom and Airbnb Places to Stay Under $200

Over 135+ Chester Varoom and Airbnb Places to Stay Under $200
Idyllic Small-Town Stay From US $135
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
2-Bedroom Retreat in Charming Small Town From US $126
         

9.7 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • View
Garner Hotel Londonderry - Manchester by IHG From US $114
         

8.6 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Stylish condo in the heart of downtown Manchester From US $123
         

Country home in city From US $63
         

10.0 (1 Review)
House
  • Parking
  • TV
  • View
Extra large 1 Bedroom apartment! From US $150
         

9.8 (8 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Chester

Over 88+ Instantly Bookable Vacation Homes in or Near Chester
Canobie Lake Hideaway From US $324
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Comfortable Studio Close to Airport/Arena/Mall
New
From US $260
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Staycation + Work From Home in one private setting From US $289
         

Charming quiet From US $314
         

9.8 (15 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Cute Mini Apt - SNHU Arena From US $238
         

9.8 (10 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

About Chester Vacation Rentals

With more than 279 Chester vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Villa Bay and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Chester.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Villa Bay Chester, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Chester. Places to stay near Chester are 466.22 ft² on average, with prices averaging $279 a night.

Villa Bay makes it easy and safe to find and compare vacation rentals in Chester with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Chester

Type Count
Holiday Apartments 111
Vacation Homes 88
Hotels with Suites 43
Cottages 14
B&B 9
Cabin Rentals 3
Others 2

Use these Quick Filters to Find a Vacation Rental in Chester

Pro Tip: Villa Bay makes it easy to compare the best listings on Villa Bay homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Villa Bay homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chester.

Weather in Chester

View the weather forecast for Chester before booking your Chester Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F