The Best Hotels for First Time Visitors in Chatham

Where to Stay on Your First Trip to Chatham

Are you looking for a hotel for your first trip to Chatham, Massachusetts? With plenty of activities and sites, this is a great destination for first-time visitors. So if you're deciding where to stay on your first trip to Chatham, don't worry, we've got you covered. We've analyzed the hotels in Chatham to find out which are the best for first timers based on price, amenities, location, reviews, and guest ratings. In this guide, we'll be showcasing the best hotels for first-time visitors in Chatham, taking into consideration all of these important factors. Whether you're traveling solo, with family, or with friends, there's a hotel that caters to every traveler's needs to make the most of your first trip here. So, if you're visiting Chatham for the first time, the hotels below will be great options, as many of them have pools, breakfast, and plenty of comforts to help you relax. So, here they are, the best hotels in Chatham for first time visitors.

(Prices are listed in U.S. Dollars.)

Chatham Bars Inn

5-star Resort with prices starting at $936 (before taxes) - See All Prices
Great Hotel for First Time Visitors

Located at 297 Shore Road, Chatham Bars Inn has great rooms from $936 (before taxes). It offers an outdoor pool, room service, a restaurant, a fitness center, and a bar. It has a terrific 8.70 rating out of 10 from previous guests who have stayed here. Only 0.5 miles from the city center, first time visitors will especially love hiking, child care, laundry services, a hot tub, and a spa at this relaxing hotel. We love the convenience of room service, and it's really nice here.

First Time Trip Hotel Amenities
  • Outdoor pool
  • Room service
  • Spa
More Great Amenities
  • Restaurant
  • Fitness center
  • Bar/Lounge
  • Hiking
  • Babysitting / Child Care
  • Laundry service
  • Hot tub
  • Free parking
  • Bicycle rental
  • Family rooms
  • Tennis
  • Refrigerator
  • Kids' club


View hotels on the map:

Chatham Wayside Inn

4-star Hotel with prices starting at $523 (before taxes) - See All Prices
Perfect for Your First Visit to Chatham
  • Heated pool

A great place to stay is Chatham Wayside Inn which has nice rooms starting at $523. Offering an outdoor pool, room service, a restaurant, a fitness center, and a bar, it also has a great guest rating of 8.60 out of 10 from many previous guests. It's located at 512 Main Street. This convenient hotel is also nice because it offers hiking, golf, free parking, bicycle rental, and family rooms which visitors will enjoy. Also, it's just 0.2 miles from the city center. You'll love relaxing in the heated pool after a busy day exploring.

First Time Trip Hotel Amenities
  • Outdoor pool
  • Room service
More Great Amenities
  • Restaurant
  • Fitness center
  • Bar/Lounge
  • Hiking
  • Free parking
  • Bicycle rental
  • Family rooms
  • Heated pool


Queen Anne Inn

4-star Hotel with prices starting at $295 (before taxes) - See All Prices
A Good Stay for Your First Trip
  • Great Value: the price is lower than average for 4-star hotels.
  • Family-Friendly
  • Heated pool

We found Queen Anne Inn to be a great place to stay, and the price starts at $295. We loved that is has an outdoor pool, room service, a restaurant, a fitness center, and a bar, and it also has a terrific guest rating of 8.30 out of 10 from previous guests. It's located at 70 Queen Anne Road. You'll also find golf, a hot tub, free parking, laundry facilities, and bicycle rental which travelers will love. And this fun hotel is just 0.4 miles from the center of town. The pool here was very nice, relaxing, and fun. It's a great value, too, because it's less than the average price for first time trip hotels.

First Time Trip Hotel Amenities
  • Outdoor pool
  • Room service
  • Family-Friendly
More Great Amenities
  • Restaurant
  • Fitness center
  • Bar/Lounge
  • Hot tub
  • Free parking
  • Bicycle rental
  • Family rooms
  • Heated pool
  • Refrigerator


Greyfinch Chatham Inn

3-star Hotel with prices starting at $351 (before taxes) - See All Prices
Perfect for Your First Time in Chatham
  • Great Value: the price is lower than average for first time trip hotels.
  • Heated pool

With terrific rooms from $351, Greyfinch Chatham Inn, at 946 Main Street provides an outdoor pool, hiking, golf, pet-friendly rooms, and free parking. Its terrific guest rating is 8.70 out of 10 from previous guests staying here. New visitors will really like this amazing hotel which also offers bicycle rental, a heated pool, a tour desk, air-conditioning, and a refrigerator. It's located just 0.6 miles from the city center, too. It's a great value, as the price is less than the average for first time trip hotels.

First Time Trip Hotel Amenities
  • Outdoor pool
More Great Amenities
  • Hiking
  • Pets allowed
  • Free parking
  • Bicycle rental
  • Heated pool
  • Refrigerator


Pleasant Bay Village Resort

3-star Resort with prices starting at $251 (before taxes) - See All Prices
Perfect for First-Timers
  • Great Value: the price is lower than average for 3-star hotels.
  • High Quality: guest ratings are higher than average.
  • Family-Friendly
  • Heated pool

Pleasant Bay Village Resort has a great guest rating of 9.30 out of 10, and offers an outdoor pool, room service, rooms with kitchens, rooms with kitchenettes, and laundry services. The great rooms here start at $251 before taxes and depending on the season. It can be found at 1191 Orleans Road. Furthermore, it also offers golf, a hot tub, free parking, laundry facilities, and family rooms, which is nice for first time visitors. Just 2.5 miles from the city center, this fantastic hotel is a terrific choice. Everyone loves a good hot tub, and this one is really nice. We found the price of this hotel to be a great value because the price is less than average for first time trip hotels.

First Time Trip Hotel Amenities
  • Outdoor pool
  • Room service
  • Kitchen
  • Family-Friendly
More Great Amenities
  • Kitchenette
  • Laundry service
  • Hot tub
  • Free parking
  • Family rooms
  • Heated pool
  • Microwave
  • Refrigerator
  • Playground


Chatham Seafarer Inn

3-star Hotel with prices starting at $267 (before taxes) - See All Prices
Among the Best Places to Stay for a First Visit to Chatham
  • Great Value: the price is lower than average for 3-star hotels.
  • High Quality: guest ratings are higher than average.

The great guest rating of Chatham Seafarer Inn is 9.10 out of 10. This place has an outdoor pool, rooms with kitchenettes, free parking, family rooms, and air-conditioning. Prices for the terrific rooms are from $267, and it's located at 2079 Main Street. We also love the a microwave and a refrigerator which are great for visitors. And since it's just 2.5 miles from the center of the town, the location is great, too. It's always nice to have a kitchenette to cook some basic meals or have an easy breakfast. The price of this hotel is less than average for first time trip hotels, which makes it a great value.

First Time Trip Hotel Amenities
  • Outdoor pool
More Great Amenities
  • Kitchenette
  • Free parking
  • Family rooms
  • Microwave
  • Refrigerator


Also, take a look at the first time trip hotels in nearby destinations: South Yarmouth, Provincetown, Falmouth, Nantucket, and Harwich.

For more terrific hotel ideas in Nantucket, make sure you also see Best Luxury Hotels in Nantucket, Best Hotels for First Time Visitors in Nantucket, Best Hotels for a Weekend Getaway in Nantucket, Best Hotels for One Week in Nantucket, Best Hotels for One Night in Nantucket, or Best Business Hotels in Nantucket.


How much do hotels for first-time visitors cost in Chatham?

Chatham Average First Time Trip Hotel Price
$437

Travelers to Chatham, Massachusetts will have a large number of terrific first time trip accommodation options with a variety of great prices. The price of first time trip hotels here can vary by amenities, dates, and the neighborhood. Based on thorough data from 6 first time trip hotels, their average price is a very reasonable $437. If you're interested in more information about hotels here, see our guide to hotel prices in Chatham.

The average prices of our suggested first time trip hotels by star rating:

  • 5-star hotels: $936
  • 4-star hotels: $409
  • 3-star hotels: $290


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