Holiday rentals in Pleasant Bay

4.95 out of 5 average rating, 21 reviews

Home in Orleans

Antique Cottage with Path to Arey’s Pond

Relax at this unique and tranquil escape. Our small but charming one bedroom cottage offers a compact kitchen and a small full bath. A true antique from 1850, the unit is updated but remains quintessential Old Cape Cod. Private yard, outdoor shower, fire pit, laundry, and access to Arey’s Pond 350 yds down private path. A pet friendly getaway for a couple looking to relax in an ideal Orleans location. Close to Nauset Beach, Orleans, Chatham, shops & great dining. A super place to vacation.

4.99 out of 5 average rating, 241 reviews

Guest suite in Chatham

Waterfront Suite on Emery Pond

Comfortably furnished studio suite w/private parking & entrance offers a garden setting w/picnic table just steps to a fresh water pond & outdoor shower. The friendly, cottage-style decor is inviting w/queen-size bed, couch, ample closets, private bathroom w/shower, small dining area w/microwave & fridge (no stove, no bbq); writing table, WiFi, Roku & DVD player. Enjoy the water view! Minutes by car to downtown Chatham. Fresh linens, bath & beach towels, shampoo/conditioner, coffee/tea. STR-46

Place to stay in Wellfleet

4.97 out of 5 average rating, 239 reviews

Romantic Cape Cod Tiny House + Hot Tub

Welcome to the Romantic Hideaway, our magical, secluded tiny house nestled between lush gardens and the woods alongside our property. Just a short drive to ocean beaches and freshwater ponds, and a pleasant walk to the quaint center of Wellfleet. Wake to birdsong and enjoy fresh muffins on your sunny, private deck. Your stay includes access to our Magnolia Spa with hot tub and sauna (June+); massage is available in July at special guest rates. A sweet, quiet escape on the Outer Cape.

4.96 out of 5 average rating, 106 reviews

Flat in Brewster

Songbird Studio- Secluded but close to everything!

Bright, sunny, secluded, green 600 sqft studio apartment at rear of Antique home in the heart of Brewster, Northside of Rt 6A. Private entrance. Private backyard with lawn & gardens. Small private deck, gas grill. Bird and small animal life abounds outside. Tons of stars at night.. salt air on the wind. Walking distance to coffee shop, convenience store, multiple restaurants, Bike Trail. Short car ride to bay beaches, easy drive to Ocean beaches. Gas "woodstove" for heat, AC for cooling.

4.88 out of 5 average rating, 258 reviews

Apartment in Brewster

Shining Sea Condo

Ocean Edge condo with cathedral ceilings! Beautiful private deck located on the 5th hole of the Ocean Edge golf course! Located within Eaton village. One king bed and one queen, along with pullout couch allows 6 to sleep comfortably. Linens are included!! Large kitchen with washer/ dryer, AC in living room and heat throughout the unit. Wifi and two smart TVs with ROKU devices. Flexible dates allows guests to stay whatever length they would like instead of a mandatory week. Come enjoy!

4.99 out of 5 average rating, 606 reviews

Guest suite in Harwich

Romantic getaway suite

GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Ten year old private one bedroom lavish suite over two car attached garage with private entrance, deck, and parking in a quiet neighborhood central to all the Cape has to offer. Beautifully furnished with central air, gas fireplace, hardwood floors, double slipper clawfoot soaking tub, separate subway tiled shower, wireless internet and Sony 49 inch 4KUHD edge -lit streaming TV.

4.95 out of 5 average rating, 241 reviews

Cottage in Eastham

The Breeze Overlooking Minister's Pond

The Breeze is a luxurious, romantic cottage by a serene freshwater pond, surrounded by vibrant gardens. Perfect for a peaceful getaway, enjoy kayaking, canoeing, and relaxing on the dock, or explore nearby trails and the Cape Cod Rail Trail with provided bikes. Unwind with evenings by the fire pit, refreshing outdoor showers, and a plush queen bed for ultimate comfort. This private oasis offers tranquility, natural beauty, and 5-star attention to detail for your perfect escape.

4.96 out of 5 average rating, 162 reviews

Flat in Brewster

Sophisticated, Private Cape Cod living

LOCATION: 3/4 mile off main road (unpaved road). Located on the town line of Brewster and Orleans with less than 5 minutes to Chatham or Harwich by car. Nauset and Skaket beaches are less than 3 miles away. Nickerson state park less than 1 mile away. Cape Cod National seashore is located within 7.2 miles of our property. Shopping on Main Street in Chatham is 15 minutes. Enjoy a nice, tranquil walk, listen to the birds or feast your eyes on the surrounding conservation land.

5 out of 5 average rating, 48 reviews

Holiday home in Chatham

Beautiful Downtown Chatham 1 Bed, Near Oyster Pond

This gorgeous home is the perfect getaway for those who want to be near downtown Chatham & the beach. Walk to shops, restaurants, the beach, a movie theater, Veterans Field for summer Chatham A’s games, The Squire, & more! This cozy, modern, & newly renovated apartment is ideal for a couple or two friends with an open living room & kitchen space + private patio. 1 Min Walk to Downtown Chatham 9 Min Walk to Oyster Pond Beach Experience Chatham with us & Learn More Below!

4.92 out of 5 average rating, 184 reviews

Guest suite in Orleans

Charming Old Cape Cod

Relax and enjoy spending time at Snowtop on the Town Cove, many activities including sailing, paddle boarding, water skiing and spectacular sunsets! A short walk to swim, sit on the sand or take a beach walk. The offered space has a private entrance with bath, bedroom with a king size bed, a sunny living room with dining table over looking the water where you could choose to dine in, have coffee in the morning or play a game.

4.92 out of 5 average rating, 267 reviews

Home in Brewster

Privacy with Cape Cod charm

This lovely, private one bedroom apartment is located above the unused garage on the grounds of our classic half cape house, just a 3 minute walk to our private beach on the bay. It sleeps 2 with a double bed and has a full kitchen and bathroom, along with an outdoor shower, grill, fire pit and picnic table located in private yard. Linens will be provided. Coffee maker and coffee will be waiting for you...

4.99 out of 5 average rating, 245 reviews

Guest suite in Orleans

Private Beach, Cozy Cape Cottage

Enjoy your own private beach with soaring seabirds and ocean breeze! Let a breathtaking sunrise and view of the bay greet you every morning from bed. Take in the waterfront view on the outside patio by the garden or in the enclosed sun porch. Escape to our cozy cottage secluded in the woods with nearby trails. Explore the Cape's many attractions and refresh your soul with a relaxing Cape Cod vacation.

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Other great holiday rentals in Pleasant Bay

4.98 out of 5 average rating, 123 reviews

Tranquil BayBreeze Private Master Suite

StephenRating, 5 stars9 months ago

This was our 2nd visit to Darlene’s and Gregs, Tranquil. Bay Breeze, which is set in a beautiful garden that’s usually full of birds. There is truly nothing negative to say. We had the same feeling of calm and relaxation as we did last year. The accommodation has everything one needs for a wonderful stay. Our hosts continue to provide lots of little touches that many other b&b’s do not. Things like toothbrush, dental floss needle and cotton repair kit, a lovely bottle of wine, scones, butter pats, fresh fruit, tea, coffee, bottle water - the list is endless! It all goes to show how Greg and Darlene care about their guests. They truly are a lovely couple. We will never tire of visiting them, their property and their lovely miniature horses.

4.85 out of 5 average rating, 102 reviews

Private room in Brewster

1750 House

JerodRating, 5 stars1 month ago

Great, cozy spot in the perfect location. Tina was so helpful and responsive!! We really enjoyed our time and the official kick off of summer! 10/10

4.93 out of 5 average rating, 191 reviews

Hillside Cape Getaway

JessicaRating, 5 stars2 weeks ago

We had a wonderful stay at Kim’s. She was very sweet and welcoming. We felt right at home! Definitely recommend staying here when visiting the cape.

4.88 out of 5 average rating, 182 reviews

Cozy Corner!

LouisRating, 5 stars3 days ago

Couldn't have asked for a better spot. Great for getting to the beach, shops, and exploring the area. Easy to get in and had everything we needed. Margie was super responsive and even let us check in early (we had a wedding to get to). I would come back and stay again, wedding or no wedding. Already planning our next visit.

4.95 out of 5 average rating, 103 reviews

Private room in Harwich

Dream Catcher 2 .Quiet room in Harwich.

GeoffreyRating, 5 stars1 week ago

Valerie and Spike were wonderful and very accommodating throughout, and that was some of the best conversation I've had in years. Thank you so much!!

4.95 out of 5 average rating, 154 reviews

Hotel room in Chatham

East Room - Chatham Guest Rooms

BonnieRating, 5 stars1 month ago

It was my husband and I’s first visit to the Cape and this space was perfect! Bob was very accomodating of our late arrival and left fantastic instructions for us to follow. He gave us great recommendations and the location was a perfect distance from Main area in downtown Chatham! (One of the days we drove and it was only 5 minutes, another day we walked (about 30 minutes) The room matched the description exactly and we really enjoyed our weekend there. Will definitely consider booking again for any future visits to the Cape.

4.92 out of 5 average rating, 103 reviews

Private room in Eastham

Knowles Farm B&B, Photo Room

TaylorRating, 5 stars1 month ago

A beautiful home in a great location on the cape, also near walking trails and amazing nature! Our room and the space designated for guests is awesome. Sarah was a great host and has fostered a wonderful community through her BnB.