Hotelaholic

Chatham · Massachusetts

Pleasant Bay Village Resort

1191 Orleans Road, Chatham, Massachusetts, 02633

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Check-in
Nov 23, 2026
Check-out
Nov 25, 2026
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HAPPI EXPERIENCE

Luxurious Amenities:: Indulge in the hot tub, outdoor pool, and game room for a relaxing stay.

  • Wellness & relaxation

    Charming Accommodations:: Enjoy private patios, free Wi-Fi, cable TV, fridge, work desk, and cozy floral décor in spacious rooms.

  • At the hotel

    Family-Friendly Features:: Kids will love the playground and table tennis while you take advantage of the on-site laundry facilities.

Book now for an unforgettable experience at Pleasant Bay Village Resort!

HAPPI HIGHLIGHTS

  • Beautiful landscaping

  • Friendly and helpful staff

  • Clean and comfortable rooms

At the hotel

Popular amenities

38 listed
  • Air conditioning
  • Allergy-free room
  • Babysitting/child services
  • Board games/puzzles
  • CCTV outside property
  • Children's playground
  • Daily housekeeping
  • Designated smoking area
  • Express check-in/check-out
  • Facilities for disabled guests
View all amenities

Pools & wellness

  • Heated pool
  • Hot tub/Jacuzzi
  • Outdoor pool
  • Outdoor pool - seasonal
  • Swimming pool

Dining & drinks

  • Kid meals
  • Special diet menus - on request
  • Wine/champagne

Fitness & outdoors

  • Garden
  • Golf course
  • Outdoor furniture
  • Sun loungers or beach chairs
  • Table tennis

Rooms & comfort

  • Heating
  • Non-smoking rooms

Safety & cleanliness

  • Safety deposit box
  • Smoke alarms

Getting around & access

  • Free Parking
  • Parking

Guest services

  • Fax/photocopying
  • Meeting/banquet facilities

Services & essentials

  • Family rooms
  • Free WiFi
  • Non-smoking throughout
  • Picnic area
  • Sun umbrellas
  • Vending machine - drinks
  • WiFi available

Review in focus

246 reviews
9/ 10
location is good
zheng · couple · 2026-09-14

The guest experience

9.7out of 10
246 verified reviews

Loved most

  • Beautiful landscaping
  • Friendly and helpful staff
  • Clean and comfortable rooms
  • Great amenities
  • Good location

Worth knowing — Not all guests experienced breakfast options · Some mention remoteness of the location

How guests scored the stay

  • Overall Experience10.0

    The overall sentiment from reviews is overwhelmingly positive and filled with enthusiasm.

  • Cleanliness10.0

    The reviews frequently highlight clean and well-maintained rooms and property.

  • Service10.0

    Numerous reviews describe the staff as helpful and friendly, contributing to an excellent experience.

  • Room Quality9.8

    Rooms are described as spacious, well-equipped, and very comfortable across multiple reviews.

  • Location9.5

    Guests mention the convenient location and accessibility to Chatham and surrounding areas.

  • Food and Beverage9.5

    Breakfast options and complementary services like free coffee are appreciated.

  • Amenities9.5

    Amenities like heated pools, hot tubs, and in-room kitchens are praised for their quality and availability.

  • Value for Money9.4

    Guests feel that the quality of the stay justifies the price, given the overall experience.

Live guest feedback

Guest reviews

Consistent

90% of 20 recent stays rated 8+

9.7246 reviews
  • Guest review

    9/10

    zheng · couple · 2026-09-14

    “location is good”

  • Good choice overall

    8/10

    Nicola · couple · 2026-09-10

    “Comfortable accommodation, staff were very helpful”

  • Guest review

    5/10

    Felix · family with children · 2026-09-10

    “Beautiful, well-maintained gardens”

  • Excellent location and overall a great place to stay.

    7/10

    Anthony · extended group · 2026-09-08

    “Room was clean and the grounds are very well maintained.”

  • Very comfortable, well located and peaceful.

    10/10

    Toni · couple · 2026-08-27

    “Clean, quiet, friendly”

  • So impressed with the variety of trees on the property.

    10/10

    Frank · couple · 2026-08-10

    “excellent”

  • Anniversary celebration

    10/10

    Q8586NCjackc · Solo travel · 2026-08-01

    “We’ve stayed at Pleasant Bay resort for a number of years celebrating our anniversary. We enjoy Chatham for shopping and restaurants.”

  • Great stay.

    10/10

    524stevens524 · Family · 2026-07-30

    “Great location. Beautiful property. Clean. Staff was fantastic. Got to feed the crazy koi in the pond. Rooms were easily accessible. Worth it.”

  • Amazing stay for a couple that went out in Chatam and Harwich

    10/10

    I1156XGmarcusp · Couples · 2026-07-28

    “Amazing experience! Did not know what to expect. Good price, great location. Off a main road but secluded by the trees. Atmosphere was so nice. the rooms so clean and they cleaned it twice a day consistently. Service and amenities were perfect. David at the front desk checking us in was so sweet. It was quiet and peaceful and great.”

  • Our favorite place!

    10/10

    Livvyreagan · Family · 2026-07-26

    “We absolutely love it here. This was our second year of staying at Pleasant Bay Village & Resort with our daughter (now two yo) and it has been the perfect home away from home both times. The rooms are very well kept with housekeeping coming twice a day (including turn down service with chocolates that thrilled our toddler). We haven’t met a single staff member that isn’t kind and welcoming. Of course, that is part of their job but it feels genuine! They’re very attentive and treat you like you matter to them or they just took the time to actually engage with my very chatty toddler. The grounds are also immaculate, have a new playground, giant koi pond (fish food at the front desk which my daughter learned quickly she could ask for) and a wonderful pool/hot tub and activity area. Having a pool is a must when visiting the cape because of weather and this one doesn’t disappoint. We also really love that they offer towel service so we’re not worrying about washing towels constantly. IThey offer breakfast and lunch (including poolside lunch service which is really a highlight). You can bring in outside food and eat by the pool - something we did for dinner a couple of nights and again the toddler loved it! The location is close (not walkable) to down town and many beaches. About an 8-10 min drive to either. If you’re looking for a low key spot in Chatham, that is also perfect for families with young kids, this is the place. Worth every penny. We can’t wait to return. Thank you to the staff for helping us make fun family memories!”

  • The best Chatham has to offer!

    10/10

    map1971 · Family · 2026-07-26

    “This place is AMAZING!!! The hospitality, rooms, cleanliness, view, pool, fish pond, restaurant, and the grounds are TOP NOTCH. The location is perfect also - near shopping, beaches, and other places but still private enough where it’s quiet and peaceful. The price was extremely reasonable and I feel it was so much more valuable than staying at other more expensive resorts. They had complimentary coffee all day, towels, and beach items you could borrow. The people were so nice. We will definitely 100% return!”

  • Wonderful Family Vacation Spot!!!

    10/10

    U4821PMmarisap · Family · 2026-07-24

    “We traveled here as a family of 4 with a 5 month old and 4 year old. It was so lovely and quiet- tons for the 4 year old to do and easy for the 5 month old to nap. We also came with my friend and her husband and three year old and my sister and brother who are about 30 and 20 respectively. My husband and I stayed in a two bedroom lower cottage with our two kids and my friend and siblings each stayed in a regular room with two queen beds. We all loved it so much we all plan to return next summer. The housekeeping was consistent and excellent- the resort was quiet and clean, and everyone was very very friendly. The pool is warm and never over crowded- the drinks and lunch at the pool are wonderful- can’t recommend this hotel enough!!! My husband wanted to rebook for next summer before we left. (All of the included pics were taken at the resort)”

  • Beautifully landscape, family, friendly, clean facility

    10/10

    Y1662XXloriw · Family · 2026-07-23

    “We had a wonderful time. It started off with David who welcomed us at the front desk, he told us all about the pleasant Valley Bay resort. He showed us around the pool gave us some tips. We went to our room, it was super clean and comfortable. The grounds were just beautiful. We fed the Koi fish. We sat by the pool. It was heated, clean warm everybody around the pool was happy with their accommodations. Many had been coming back for years, which says a lot for the establishment. We stayed the next day until it was lunch, which was not overpriced and very good, even though we had checked out. we were really impressed and glad that we stayed and will be back.”

  • Hotel was secluded and quaint, clean & quiet. The grounds were immaculate and the staff couldn't go out of their way more for th

    10/10

    E3693TPkathrync · Solo travel · 2026-07-21

    “Hotel was secluded and quaint, clean & quiet. The grounds were immaculate and the staff couldn't go out of their way more for their guests.”

  • Charming Cape Cod Resort

    10/10

    gaylenela · Family · 2026-07-20

    “Pleasant Bay Village Resort was a recommended hotel option for a Cape Cod wedding I was attending. It came highly recommended by a local, and it did not disappoint. It was conveniently located to the wedding activities, as well as the fish market & Main St. shopping. All were just a short car ride away. The rooms are updated, charming & well-maintained. The grounds have lush landscaping & are a feature in and of itself. The pool was a refreshing gathering space for family & friends. I would stay again & highly recommend!”

  • Best Cape Cod Resort

    10/10

    rogervH8451QE · Family · 2026-07-20

    “We loved Pleasant Bay! The staff was friendly and always helpful and cheerful. The rooms were spotlessly clean and well appointed. The lobby had the look of an old New England inn. The gardens, coy pond the whole grounds were well manicured. The pool was great, too. Everything was beyond expectations! Thank you Pleasant Bay for a great experience!”

  • A true gem !

    10/10

    Tinamaje · Family · 2026-07-20

    “A true gem - beautiful landscaping with a Koi pond & multiple mini waterfalls which add to the sense of tranquility. We stayed in a 1 bedroom cottage - immaculately clean, high quality kitchen, effective air conditioning and very comfortable loungers on the back porch. Perfectly located close to Chatham. The most welcoming & friendly staff - Peter and Josh always keen to share helpful tips and advice. We enjoyed relaxing by the pool after sightseeing each day - pool towels provided. Complimentary tea & coffee available at reception. Special thanks to Joe for resolving the issue with our fridge freezer- he even brought a new mini fridge just in case - that’s customer service ! A small self service laundry room with 2 washers ($2 per wash) & 2 dryers (25c per 5/mins). Highly recommend!”

  • Consistently Amazing

    10/10

    VetGirl1982 · Family · 2026-07-11

    “This is our fourth trip to the resort and I find it to be one of the most consistently excellent places I have had the privilege to visit. Walking into our cottage always feels so welcoming and refreshing. Housekeeping has everything immaculate and all we have to do is bring in our bags to feel at home. Every time I leave, I find myself wondering when the booking window opens for the following year.”

  • Peace Amongst Cape Cod Crowds

    10/10

    guyandlizzyb · Family · 2026-07-09

    “Pleasant Bay Village was quiet, clean and comfortable. The staff was the absolute BEST, very accommodating. We will stay there the next time we’re on the Cape!”

  • Another great vacay

    10/10

    Curiosity14266866806 · Family · 2026-07-08

    “As usual we had a fantastic time at Pleasant Bay. At this time I’d say we’ve been back 10 or 12 times. The people are wonderful, the grounds are beautiful, the location can’t be beat. The accommodations are remarkable. Some rooms are pet friendly and you’d never know there had been a pet in them before your own! Hope to return at least once more this summer!”

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Hotel info and reviews come from third-party sources.