Search Deals on
Chesterwood Vacation Packages

Chesterwood Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Latham Albany Airport

Baymont by Wyndham Latham Albany Airport

2.5 out of 5
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Albany (ALB)
Book a stay at this business-friendly hotel in Latham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.
The Manchester View

The Manchester View

2.5 out of 5
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
Stay at this hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dana L. Thompson Memorial Park and Lye Brook Falls are located nearby.
Kimpton Taconic Hotel, an IHG Hotel

Kimpton Taconic Hotel, an IHG Hotel

4 out of 5
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
Stay at this 4-star golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Albany (ALB)
Book a stay at this business-friendly hotel in Latham. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.
Hilton Albany

Hilton Albany

3.5 out of 5
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Albany (ALB)
Book a stay at this business-friendly hotel in Albany. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions MVP Arena and The Egg are located nearby.
The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Albany (ALB)
Stay at this 4-star business-friendly hotel in Schenectady. Enjoy free WiFi, free parking, and 5 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Rivers Casino & Resort and Museum of Innovation and Science are located nearby.
La Quinta Inn & Suites by Wyndham Clifton Park

La Quinta Inn & Suites by Wyndham Clifton Park

2.5 out of 5
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Albany (ALB)
Stay at this hotel in Clifton Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Clifton Common and The Edge Halfmoon are located nearby.
Microtel Inn by Wyndham Albany Airport

Microtel Inn by Wyndham Albany Airport

2 out of 5
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Albany (ALB)
Book a stay at this business-friendly hotel in Latham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.
Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Albany (ALB)
Book a stay at this business-friendly hotel in Albany. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.
The Century House, Ascend Hotel Collection

The Century House, Ascend Hotel Collection

3 out of 5
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Albany (ALB)
Stay at this 3-star business-friendly hotel in Latham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Colonie Center Mall and Latham Farms are located nearby.
Homewood Suites by Hilton Saratoga Springs

Homewood Suites by Hilton Saratoga Springs

3 out of 5
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Albany (ALB)
Stay at this 3-star business-friendly hotel in Saratoga Springs. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Saratoga Performing Arts Center and Saratoga Race Course are located nearby.
Comfort Inn Glenmont - Albany South

Comfort Inn Glenmont - Albany South

2.5 out of 5
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Albany (ALB)
Book a stay at this business-friendly hotel in Glenmont. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions The Egg and MVP Arena are located nearby.

3-4 Night Vacations in Chesterwood

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Clifton Park

La Quinta Inn & Suites by Wyndham Clifton Park

2.5 out of 5
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Albany (ALB)
Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Albany (ALB)
Hilton Albany

Hilton Albany

3.5 out of 5
Downtown Albany
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Albany (ALB)
The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Stockade Historic District
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Albany (ALB)

5-7 Night Vacations in Chesterwood

Price found within the past 48 hours. Click for updated prices.
The Manchester View

The Manchester View

2.5 out of 5
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
Kimpton Taconic Hotel, an IHG Hotel

Kimpton Taconic Hotel, an IHG Hotel

4 out of 5
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
Homewood Suites by Hilton Saratoga Springs

Homewood Suites by Hilton Saratoga Springs

3 out of 5
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Albany (ALB)

Chesterwood Last Minute Hotel Deals

The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
Stay at this 3.5-star spa hotel in Stockbridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the property ...
The Red Lion Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 out of 5
26 Glendale Road, RR 183, Stockbridge, MA
Stay at this 4.5-star luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Chesterwood ...
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Tanglewood Suites
Tanglewood Suites
2.5 out of 5
MA-102, Stockbridge, MA
Stay at this B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Naumkeag Museum are located ...
Tanglewood Suites
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
3.5 out of 5
190 Meadow Street, South Lee, MA
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our ...
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
The Little Lion
The Little Lion
3 out of 5
506 Stockbridge Road, Great Barrington, MA
Stay at this 3-star motel in Great Barrington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
The Little Lion
Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge
2 out of 5
42 Stockbridge Rd, West Stockbridge, MA
Stay at this motel in West Stockbridge. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions ...
Pleasant Valley Motel West Stockbridge
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
3 out of 5
Great Barrington
Stay at this 3-star cottage in Great Barrington. Enjoy free parking, in-room fireplaces, and housekeeping. Popular attractions Art et Industrie and Chesterwood ...
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
The Inn at Stockbridge
The Inn at Stockbridge
4 out of 5
30 East Street, Lee, MA
Stay at this 4-star B&B in Lee. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and National Shrine of the Divine ...
The Inn at Stockbridge
See all 689 properties in Chesterwood
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Book the perfect getaway to Chesterwood

With Hotwire, booking your next trip to South Lee is a breeze. When it comes to planning a show-stopping vacay, you’re the reigning champion of doing it on a dime. You love to plan exciting destination adventures while saving money on a budget.

Hotwire is here to help you plan a smooth sailing trip to Chesterwood while saving some major cash. Doubling up on vacation expenses like hotel and car rentals and fun-filled excursions can save you money—especially when you book one of Hotwire’s vacation packages.

If your trip to is spur-of-the-moment and you’re leaving soon, Hotwire can save you up to 60% off your rentals with Hotwire Hot Rate deals. Book with Hotwire to grab a stellar Chesterwood flight and hotel package for as low as $533.

Living it up in South Lee means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s Chesterwood, South Lee vacation packages to enjoy the best of both worlds. Flight and hotel packages typically include roundtrip non-stop flights and multi-day hotel stays. Packages are priced per person and are perfect for flying solo or traveling with a group of friends or family. Conveniently choose from Hotwire’s inventory of hotels in Chesterwood for some of the best accommodations and flight deals.

FAQs about cheap Chesterwood packages:

How to get cheap vacation deals to Chesterwood?

Save up to 60% off vacation deals with Hotwire Hot Rates. Just plug in your general preferences and let Hotwire choose matching hotels for as low as $70.

How much are Chesterwood packages?

Vacation packages to Chesterwood vary in price. They are priced per person and include discounted hotel and flight costs. With Hotwire, you can score a vacation package for as low as $533.

How to find cheap car rentals near Chesterwood?

Hotwire partners with some of the most reliable car rental companies in South Lee to bring you the best car rental deals in Chesterwood for as low as . Select a rental from Hotwire’s extensive inventory of cars for every travel style. If you plan on bringing friends or family along, opt for a spacious SUV. If you’re visiting on business but still plan to make time for off-the-clock adventures, Hotwire offers sleek luxury and convertible rentals.

Is it safe to travel to Chesterwood now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Chesterwood right now?” When it’s time to book your vacation, check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.