Holiday rentals in Oyster Pond

5 out of 5 average rating, 18 reviews

Red Door Retreat in Chatham is 80% full for summer

Grab 1 of the last 2 summer weeks of 2025 before they're all gone at this beautiful 3bed/2.5 bath house. Cathedral L/R w/fireplace. Sunroom w/sectional and 65" TV. Dining room table for 9. Queen guest room plus "kids" bedroom with twin/full bunks & addl twin. King suite w/daybed, tv, & office area. Loft w/60" TV & Queen Sleeper. Water view deck w/dining table. Pool Table, Ping Pong, Shuffleboard, Outdoor shower, W/D, bikes, BBQ, Solo fire pit, kayaks, Wifi, A/C, Kid's gear, Access to Oyster Pond

4.99 out of 5 average rating, 240 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

5 out of 5 average rating, 9 reviews

Luxury Home- Chatham Center- Walk to Town + Beach

Enjoy easy access to everything from this centrally located condo in the heart of downtown Chatham. This luxury condo is perfect for families, couples, or a group of friends looking to be walking distance to restaurants, boutiques, the beach & so much more! Enjoy an extremely spacious home with almost 2,700 sq ft of living space, 3 ensuites, & a large roof deck. In Downtown Chatham .3 Miles to Oyster Pond .5 Miles to Seaside Links Golf Course Experience Chatham with us & learn more below!

4.97 out of 5 average rating, 373 reviews

Guest suite in Brewster

Sheep Pond Get-Away

The AirbNB Studio Space is Private w/ its own separate entrance & exit. Our home is set in the 'Sheep Pond' area. We are walking distance to Sheep Pond to kayak & swim. We have kayaks, paddleboards, beachchairs, & towels for your use. A backyard w/ your own picnic table, seating area, & hammock. An outdoor shower ! Minutes away from bay & oceanside beaches, biking, hiking & Nickerson State Park. 40 mins from Provincetown; & surrounded by quaint Route 6a, restaurants & shopping !

Place to stay in Wellfleet

4.97 out of 5 average rating, 237 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.

4.99 out of 5 average rating, 605 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.

4.97 out of 5 average rating, 263 reviews

Flat in Chatham

The Knoll

A quiet home nestled next to conservation land at the end of a dirt road. Though there are neighbors, the landscaping creates a private oasis. The downstairs apartment with private entrance is old New England with Cape Cod affects. The Bedroom has a queen bed. Second sleeping area has a Daybed with trundle and is partially open to the living area. Outside deck has a grill and shower for guest use. Close to School House pond, bike path, and 3 miles from beaches, shopping, and downtown.

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!

4.95 out of 5 average rating, 59 reviews

Cottage in Chatham

Renovated Chatham Windmill! Walk to Beach/Town!

Newly renovated Chatham Windmill! Beautiful Water View, Steps to Oyster Pond Beach & Main Street! Complete renovation of Windmill in 2022. This unique rental has one bedroom with king bed on second floor, with small full kitchen/dining area, two sitting/TV areas and full bathroom on first floor. Private patio with BBQ grill, dining table and chairs. Enjoy the beautiful water view from Adirondack chairs, just outside your door! Perfect spot for your vacation!

4.96 out of 5 average rating, 332 reviews

Apartment in Chatham

In-town, Pied-a-Terre. Private, Sunny Urban Oasis

Bright, Sunny, great in-town location. CLEAN, SAFE & PRIVATE and spacious, hidden ABOVE shops, behind the Main Post Office. Great for Romantic Getaway, WEDDING GUESTS, business trips, overflow guests or just a quick get-away break. Comfortably furnished, thoughtfully outfitted. Full Kitchen, Quality linens, duvet etc. Walk to everything. Private parking. **Please Note: Additional MA lodging tax of 12.45% will apply to all short term rentals**

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.

4.91 out of 5 average rating, 186 reviews

Quaint Downtown Chatham Home

This charming and totally renovated Chatham home is on a private road in a downtown neighborhood of exclusive homes. Its ideal location enables you to walk to Lighthouse Beach about (1/2 mile) and 1 block from downtown Chatham. Also, the house is a quick walk to Children's Beach (Oyster Pond).

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Other great holiday rentals in Oyster Pond

4.93 out of 5 average rating, 191 reviews

Private room in Orleans

Hillside Cape Getaway

JessicaRating, 5 stars1 week 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.

5 out of 5 average rating, 5 reviews

Flat in Chatham

Chatham Studio- .5 mile to beach

RogerRating, 5 stars8 months ago

A great stay to base out of to explore Chatham and lower Cape. Tom was very helpful and responsive.

4.95 out of 5 average rating, 75 reviews

Cottage in Chatham

Chatham Rose Arbors Artist Cottage

KimRating, 5 stars7 months ago

My husband and I came to Chatham for a long weekend to celebrate our wedding anniversary. This cottage is perfect for a couple and was very clean. A charming space with enough room for two, a stocked kitchenette, a comfy bed, and a spacious place for your bikes and outdoor things. Danielle and Brett provided two bikes, but we brought our e-bikes which were incredible for cruising around. We thoroughly enjoyed traveling along the amazing rail trails, which were super close by. Each morning we enjoyed the delicious coffee that was provided from Snowy Owl (loved grinding our own beans-the aromas were incredible) and also the fantastic local recommendations given to us by our hosts. They have a guitar which my husband played, making us feel right at home. We highly recommend this adorable clean bright space for a romantic getaway in lovely Cape Cod. It was close to everything and we loved being so close to “home” after dinners out in Chatham. 10 out of 10!!

5 out of 5 average rating, 7 reviews

Chatham Cape Cod Retreat

KatyRating, 5 stars9 months ago

Kim’s home was absolutely beautiful and perfectly clean! We enjoyed all the amenities and appreciated having a very well equipped kitchen with everything we could need. Couldn’t ask for a better airbnb, we will definitely be back!

4.96 out of 5 average rating, 179 reviews

Hotel room in Chatham

Main Suite - Chatham Guest Rooms

PatriciaRating, 5 stars2 weeks ago

What a fabulous stay in Bob’s beautiful apartment! This was my second visit, and I wouldn’t stay anywhere else. The spacious apartment is immaculately clean and very well appointed - Bob has thought of everything, and it is full of lovely touches. Very comfortable bed, cozy living room with a great library, well-equipped modern kitchen, a full-sized washer and dryer, and a wonderful bathroom with lots of storage. Bob is a very responsive host, and this charming accommodation gets my very highest recommendation!!

4.95 out of 5 average rating, 102 reviews

Private room in Harwich

Dream Catcher 2 .Quiet room in Harwich.

GarrettRating, 5 stars1 week ago

I was really pleased with this one- it had a very very calming vibe( im highstrung so that says alot) i slept well and felt really at home.

5 out of 5 average rating, 8 reviews

Flat in Chatham

Private Basement one bedroom in owner occupied

BriRating, 5 stars10 months ago

Jamie was a friendly, excellent communicator from the beginning. We found her home easily and checked in via key pad. The unit looks like the pictures. She had all of the essentials and then some including beach towels, beach chairs, and even a bike/helmet that we borrowed. A few things to note: there is no separate bedroom in the sense that there isn't a door to separate the two spaces that have beds. It was still fine for us and the rooms are separate but not closed off. Also it's a basement so there are some spiders as you'd expect. Overall it was a perfect launching point for our Cape stay- walkable to downtown and easily driveable to the rest of the Cape while having the right essentials for us. Our only regret is not being able to join Jamie for a bbq!