Chatham Vacation Packages 2025/2026 from $407

Chatham flight + hotel vacation packages

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

Stonybrook Motel & Lodge

Save 100% on your flight

per person

Sep 23 - Sep 27

found 1 day ago

Roundtrip non-stop flight included

Tampa (TPA) to Burlington (BTV)

An indoor pool, free self parking, and barbecue grills are featured at this motel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A garden, a lobby fireplace, and a picnic area are also on offer.

Cold Spring Plymouth Resort

Save 100% on your flight

per person

Oct 1 - Oct 6

found 6 hours ago

Roundtrip flight included

Tampa (TPA) to Manchester (MHT)

A golf course and an outdoor pool are featured at this vacation home. Enjoy the indoor pool and perks like free WiFi. There's a gym on site, and laundry facilities and barbecue grills are also offered.

Outbound Stowe

Save 100% on your flight

per person

Oct 18 - Oct 22

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Burlington (BTV)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the hot tub and perks like free self parking and free WiFi. A terrace, a garden, and a lobby fireplace are also on offer.

The Centennial

Save 100% on your flight

per person

Sep 23 - Sep 27

found 1 day ago

Roundtrip flight included

Tampa (TPA) to Manchester (MHT)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 4 conference rooms, free WiFi in public areas, and express check-out. Guests will appreciate freebies like continental breakfast and free self parking.

Club Wyndham Smugglers’ Notch Vermont

Save 100% on your flight

per person

Oct 18 - Oct 22

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Burlington (BTV)

A water park, 9 restaurants, and 8 outdoor pools are all featured at this smoke-free hotel. There's a free ski shuttle, and ski lessons, ski rentals and ski passes are available on site. Bring the family and enjoy the children's club, mini golf, and children's pool.

Top Chatham hotels deals

Green Granite Inn, Ascend Hotel Collection

1515 White Mountain Hwy, North Conway, NH

Free Cancellation

Reserve now, pay when you stay

$81 nightly

$88 total

Sep 8 - Sep 9

Total includes taxes and fees

This hotel features an indoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking.

Pool

Breakfast included

North Conway Mountain Inn

2114 White Mountain Highway, North Conway, NH

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$107 total

Aug 19 - Aug 20

Total includes taxes and fees

Free WiFi in public areas is available at this motel. Take advantage of the free self parking.

Parking included

Free WiFi

North Conway Grand Hotel

72 Common Court, North Conway, NH

Free Cancellation

Reserve now, pay when you stay

$177 nightly

$193 total

Sep 15 - Sep 16

Total includes taxes and fees

This hotel features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

Pool

Hot Tub

Omni Mount Washington Resort & Spa

310 Mt Washington Hotel Rd, Bretton Woods, NH

Free Cancellation

Reserve now, pay when you stay

$249 nightly

$270 total

Sep 4 - Sep 5

Total includes taxes and fees

This smoke-free resort features a golf course, a full-service spa, and a nightclub. There's a free ski shuttle, and ski lessons, ski rentals and ski storage are available on site. Families will appreciate the arcade/game room and picnic area.

Pool

Spa

Town and Country Inn & Resort

20 State Route 2, Gorham, NH

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$130 total

Sep 8 - Sep 9

Total includes taxes and fees

This motel features an indoor pool, a hot tub, and a restaurant. Enjoy the sauna and perks like free self parking and free WiFi. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.

Pool

Hot Tub

Grand Summit Hotel at Attitash

104 Grand Summit Road, Bartlett, NH

Free Cancellation

Reserve now, pay when you stay

$124 nightly

$135 total

Sep 16 - Sep 17

Total includes taxes and fees

Ski-in/ski-out access and an outdoor pool are featured at this smoke-free hotel. Take advantage of ski passes and ski storage on site. Enjoy a meal from the restaurant and perks like free self parking and free WiFi.

Pool

Parking included

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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.

Popular places to visit

Baldface Range

Enjoy a trip to Baldface Range and popular activities like hiking in Chatham. Discover the mountain views in this quaint area, or enjoy its ski slopes.

Sherman Farm

You can learn about the history of Center Conway with a trip to Sherman Farm. Make time for the shops and ski slopes in this family-friendly area.

Frequently asked questions

How much are vacation packages to Chatham?

Your travel daydreams can come to life in Chatham for as low as $407. Package deals include flights and hotels, and they'll make booking your trip easy as pie. All you'll have to worry about is getting out there and having a great time.

Where can I get the best vacation package deals for Chatham?

Head straight to Travelocity. With access to 400 air carriers and an impressive 1,000,000 hotels around the world, selecting the ultimate Chatham package deal couldn't be easier.

Why should I purchase my Chatham vacation bundle with Travelocity?

Travel is all about making fantastic new memories and leaving all your stresses behind — which is why we provide you with a friendly team of customer service experts available round-the-clock should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best deal available on our superb range of getaway packages. So what are you waiting for? There's no time like the present to secure that vacation you've always dreamed of.

Will I save money on my Chatham car rental if I bundle it with a hotel or flight?

Bundling your car, flight and hotel into a Chatham vacation package is a surefire way to land the best deal. Plus, having your own rental car gives you freedom to get to all the landmarks you're eager to explore. Sitting 120 mi away from Chatham, Harvard Square is one place that should have a place on your itinerary. Buckle up and make a day trip of it.

Which airport is best for Chatham?

Chatham has a couple of airports to fly to — Portland Intl. Jetport Airport (PWM) (50 mi away from the city center) and Augusta State Airport (AUG) (60 mi away from central Chatham).

Where should I stay when visiting Chatham?

The A Hiker's Haven in The White Mountains A cozy cottage with breathtaking view's is recommended by many travelers. Book as soon as possible before it's too late.