Hotel vacation rentals in Dennis

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Top-rated hotel rentals in Dennis

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Top guest favorite
A view from a balcony showcases a wide stretch of ocean under a clear blue sky. Outdoor seating arrangements are visible below, along with a pathway leading to the beach. A few seaside homes can be seen in the distance.
Hotel room in Dennis Port
5 out of 5 average rating, 9 reviews

Oceanview condo with heated pool

NOTE: QUEEN BED SHEETS AND TOWELS NOT PROVIDED. You won’t want to leave this charming, one-of-a-kind place. This 2nd floor condo has a large deck which overlooks the ocean and a heated pool. Onsite management for all your needs during your stay. Gas grills and outdoor seating for your meals. Spend the day across the street at the beach, grab a bite to each at many area restaurants, and take a dip in the heated pool. Sofa bed in living room for additional guests (4 guests total allowed).

Superhost
A spacious room features a modern bed with a white quilt and decorative pillows. A small desk with two chairs is positioned against the wall, accompanied by a refrigerator and air conditioning unit. Nautical-themed decor and a round mirror enhance the ambiance.
Hotel room in Vineyard Haven
4.61 out of 5 average rating, 92 reviews

Boutique motel w/ private beach, steps from ferry

Lovely, modern room in boutique hotel with private beach. Watch the Steamship Authority ferries come into the harbor. No need for a car as the property is just steps from the ferry terminal, art galleries, shops and restaurants like the famous Black Dog Tavern. Unit was completely remodeled in 2021 featuring all new furniture and decor. The property offers friendly service and amenities such as outdoor grill, picnic tables, beach loungers, and a community room. A perfect island getaway!

Guest favorite
A cozy sitting area features two comfortable black chairs flanking a small wooden table. Natural light filters through multiple windows adorned with patterned curtains, while a window seat showcases decorative cushions. A coffee maker is positioned on the side table, adding convenience to the space.
Hotel room in Chatham
4.96 out of 5 average rating, 164 reviews

East Room - Chatham Guest Rooms

This comfortable unit consists of a large bedroom with high ceilings and exposed beams, a comfortable sitting area, one queen-size bed, and a window seat. The East Room sleeps 1-2 people, and includes a private bath, air conditioning, a television (basic cable), a coffee maker, and a minifridge. Children accompanied by an attentive adult must be at least 7 years old. This unit is upstairs. Stairs in old buildings are steeper than modern stairs. Best for guests comfortable with stairs.

Guest favorite
A charming Victorian house featuring intricate woodwork and a wrap-around porch adorned with floral elements. Large windows allow natural light to flood the interior. The second floor includes a balcony with decorative railing, enhancing the building's character. Lush greenery surrounds the property.
Hotel room in Oak Bluffs
4.89 out of 5 average rating, 44 reviews

Porch Room 1 queen bed

The Porch Room has a queen bed and private shower room and half bath located next door to the room in the hallway. This bedroom also has its own entrance to the wrap around porch. The Porch room is one of six rooms at the Tivoli Inn. The Tivoli Inn is a charming Victorian Gingerbread house which has the island charm and a clean and friendly atmosphere. The inn is walking distance to all downtown amenities including town beach, seasonal ferry terminals and public transportation.

Superhost
The small motel features a charming exterior with a welcoming entrance. Lush trees with vibrant autumn leaves surround the property, providing a serene backdrop. The asphalt drive leads to individual rooms, enhancing a private and tranquil atmosphere.
Hotel room in Sandwich
4.59 out of 5 average rating, 622 reviews

Boutique 1950s Cape Cod motel

We are a small 1950s motel in a tranquil setting. You drive up to your room. We offer breakfast, housekeeping, and have guest laundry and vending and ice. Every room has a frig, microwave, coffee and tea service, and bath amenities. We offer suites with kitchenettes but these you book directly with us. You have to be 21 to rent a room, we are no pet-friendly, and 100% non-smoking. There are places to smoke. Office is open 6am-10pm. You can check-in after, just let us know.

Top guest favorite
Private room in Chatham
5 out of 5 average rating, 32 reviews

Tina's Culdesac B&B Sleeps 4 w/ Breakfast

Our Bed and Breakfast is at the end of a quiet cul-de-sac. The neighborhood is quiet, beautiful, well maintain, and within walking distance of local beaches, the fish pier and downtown Chatham where you can dine and shop. The Innkeepers will serve you a continental breakfast each morning. We will clean your room while you are out and about each day. We are also very knowledgeable about great places to eat, shop, or where to go to the beach.

Top guest favorite
A freshly renovated room features a spacious bed adorned with neutral-toned linens. Natural light filters through two bright windows. A private bathroom with a shower is visible through an open door, complementing the serene green walls.
Hotel room in Wellfleet
4.89 out of 5 average rating, 197 reviews

Wellfleet Center Oasis Room 1

Beautiful, newly renovated room with connected private bath in lovely downtown Wellfleet private home. Room includes TV, Microwave & Mini Refrigerator This much sought after town location gives you the freedom to walk to shops, restaurants, galleries, public transportation, town pier and bay beach. This quiet location is just one short block to Main Street. (PLEASE NOTE: We are unable to accommodate infants, children and pets.)

Superhost
A welcoming entrance is framed by manicured greenery and features a series of steps leading up to double glass doors. A brick pathway guides visitors to the front porch, which is illuminated by pendant lighting.
Hotel room in Chatham
4.94 out of 5 average rating, 18 reviews

Serene retreat with pool & fitness center

A daily resort fee of $35 per room is collected by the hotel. At Chatham Wayside Inn, our newly renovated rooms offer guests a warm, inviting atmosphere in two distinctive buildings—the Main Inn and Parkside—centering around a serene patio and pool. Each of our 56 rooms and suites features its own unique décor and special touches. We take pride in providing a comfortable, refreshed stay designed for relaxation and enjoyment.

Guest favorite
A soft, inviting bedroom is highlighted by a spacious bed dressed in white linens. Two decorative lamps with ornate bases sit on either side of the bed, illuminating plush pink pillows against a light-hued headboard. A framed mirror above the bed reflects natural light.
Hotel room in Falmouth
4.92 out of 5 average rating, 72 reviews

Park Side Queen Room @ Frederick William House

This beautifully appointed room with private bath & sitting area, includes bike rentals, cable, free WIFI, overlooking gardens & park. We are located on the Shining Sea Bikeway in Falmouth, across the street from Goodwill Park, a short walk to the Steamship Authority. Guest are welcome to take bikes over to Martha's Vineyard for day excursions. Beach passes are available, 139 private & public beaches to choose from.

Guest favorite
Aerial view of the Briarwood Beach Motel grounds showcases a well-maintained expanse of green lawn. A large American flag stands prominently at the forefront. Colorful lounge chairs are arranged on the lawn, while the motel building is visible in the background, surrounded by trees.
Hotel room in Weweantic
4.76 out of 5 average rating, 25 reviews

Briarwood Beach Motel

Briarwood Beach Motel Just minutes from Cape Cod, our Motel is situated right on the water with unbelievable views / sunsets. We are a short walk from great New England restaurants with fresh seafood and drinks. Local hiking trails can be found close by, as well as a water park. Fish from the shore or launch a kayak into the Weweantic River right from the property!

Superhost
The exterior of The Coonamessett showcases a charming blend of red buildings with white trim under a cloudy sky. A welcoming entrance is visible, framed by lush greenery and colorful flowers. An American flag stands proudly near the entrance, complementing the classic New England architecture.
Hotel room in Falmouth
4.75 out of 5 average rating, 4 reviews

In the “village” behind the main inn building

Stay in our cozy, dog-friendly Village King Suites near Jones Pond, behind our Falmouth MA inn. Each 375-square-foot suite features a separate king bedroom, living area, walk-in shower, and modern amenities like two Smart TVs, mini-fridge, and free WiFi. Accommodates up to three guests with a roll-away bed. Perfect for guests traveling with pets!

Top guest favorite
A comfortable bed is dressed in a light-patterned coverlet, flanked by a vibrant red pillow featuring an anchor design and a decorative pillow with the word 'ahoy'. A mirror with a mermaid decoration hangs above the headboard, with soft blue walls enhancing the space.
Hotel room in Hyannis Port
4.86 out of 5 average rating, 115 reviews

#8 location location location, pool private room

Private rooms, private bath, wifi, continental breakfast daily at Salt Winds. Walk to beach and town and enjoy all Hyannis has to offer. Island ferry one mile to both Islands, 1 hour drive to PTOWN. Parking, pool no glass in pool area, beach towels and chairs available. Other rooms available sorry no pets allowed

Popular amenities for Dennis hotel rentals

When is the best time to visit Dennis?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$94,224 GYDG$97,149 GYDG$97,149 GYDG$101,746 GYDG$67,064 GYDG$81,898 GYDG$102,164 GYDG$100,074 GYDG$78,346 GYDG$83,778 GYDG$94,224 GYDG$94,224 GYD
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Quick stats about hotel rentals in Dennis

  • Total vacation rentals

    Explore 60 vacation rentals in Dennis

  • Nightly prices starting at

    Dennis vacation rentals start at G$20,892 GYD per night before taxes and fees

  • Verified guest reviews

    Over 340 verified reviews to help you choose

  • Vacation rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Dennis vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Dennis rentals

  • 4.7 Average rating

    Dennis stays receive an average rating of 4.7 out of 5 from guests

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