
Condo vacation rentals in Dennis
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Top-rated condo rentals in Dennis
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Popular amenities for Dennis condo rentals
Weekly condo rentals

Seaview Cottage
Great place to stay with a short walk or drive to nearby beaches. We didn’t spend a whole lot of time at the place since we wanted to get out on the water and explore.

Stylish Onset Condo: Beach Downtown Monthly Rates
This BNB was cute, clean and walking distance to a lot of restaurants, coffee shops, store and mainly the beach. The host quickly responded to some questions we had. He even called to answer a question that we had. We loved this place. Nice TV's in all rooms. Clean bathrooms and kitchen. We will definitely stay here again when we return.

Sleek 1BR Oceanfront | Deck | Washer/Dryer
Large space, clean, and great location! Walking distance to awesome restaurants and right on the beach.

Ocean Edge 2 Bed 2 Bath, Golf & Free Resort Access
We enjoyed a beautiful weekend in Brewster at Chris’s place. The accommodations were perfect for our family of six, and we really appreciated having two full bathrooms. The condo had ample space for family meals and board games, and the location is terrific—adjacent to the golf course and walkable to pickleball courts.

LOCATION LOCATION!! Ocean- View TOP Floor Condo
Heather's place is beautiful! An amazing location with close proximity to the OB steamship authority station, a number of bus lines, and the beach! The view and location are unbeatable! Heather was also super responsive in terms of coordinating flexible check-in/check-out times which was very much appreciated. Overall, would definitely recommend to anyone visiting OB :)

Stunning Waterfront Condo-Prime Spot w/ Parking!
The location was spectacular and the unit was clean and spacious. We loved it!

Lovely two-bedroom condo in Brewster MA!
Wonderful stay !! Nick’s place was absolutely perfect for us. It was immaculate with very comfy beds, well stocked kitchen, beach chairs and towels too. It really had everything we needed! Nick was very responsive and accommodating, would not hesitate to stay here again !!

Beach Cottage 3nts/4th Free in August,Mashpee MA
Our second visit. We love the place. Quiet but close to great beaches and the Popponesset Marketplace is 2 minutes walk away, with fish restaurants and small stores with necessities (including wine and beer!). A highlight of this visit was sitting on the patio in the morning and 3 times seeing an osprey dive to the pond and catch a fish.
Pet-friendly condo rentals

557 Route 28, Unit 201, Harwich Port Cape Cod
This rental is absolutely stunning! We had such a wonderful time!! Coffee shop right under us was a special treat! Walking distance to everything - little walking path to get you to the beach and get very clean! Large space, clean, and comfortable! One heads up- clean sheets and towels are in laundry bags when you get there make your own bed and put out towels!

Short Walk into Town - Nice Comfortable Reasonable
Walkable to all local shops. Unit was clean and the kitchen was fully stocked with all items needed to prepare and enjoy a meal.

Crow's Nest Down Town New Bedford.
Phil's place is ideally located in New Bedford for beautiful walks along the pier and throughout the downtown historic district. Close to great restaurants and coffee shops. The crows nest offers the best views of the downtown! Phil was very helpful and responsive. Easy to get checked in and out.

Seaside 2 BR Condo (111-5)
Perfect location right near the beach, cosy place to stay with everything we needed to be comfortable. Loved it!

Private 3bdrm Condo Tashmoo Woods
Barbara’s condo was roomy and comfortable. We fell in love with the screened in porch. Lovely room for a cup of coffee in the mornings and a glass of wine in the late afternoon. We took a short ride through the woods to the town beach which led us to beautiful views of Tashmoo. We had a great time!

Beautiful New 2 Bed 2 Bath Condo
The place was just as the pictures showed and is in a great location. Easy in and out to the highway yet quiet in the evenings. The backyard is very roomy and a nice feature at the end of the night. I'd recommend David's place.

2BR dog-friendly 2-story condo with community pool
Very nice, clean, efficient and well located. Will definitely rent here again next time in the area visiting family.

Apartment in East Orleans Historic Home
A very nice clean and peaceful place close to beaches and restaurants. Looking forward to coming back again soon.
Condo rentals with a pool

Cozy Studio Just Steps Away From the Beach!
Perfect little studio for two people! Great location - close to beaches and restaurants and there’s even a pool! Michael was super responsive and the place was exactly like the pictures!

1BR 2nd Floor Condo with pool
Amazing stay!! Me and my best friends had a great weekend away!!!! Keith was great!!! Would 100% recommend!

Comfy Cape Escape! Spacious, Cozy, Close to Beach!
Wonderful beach location. We enjoyed the local walkable beaches and restaurants. Close to anywhere in the cape , we had a great trip.

Ocean Edge: 2 bed/2 bath - Pools & Resort Access
Had a great weekend at Josh’s place! Smooth booking process, great communication, easy checkin. The space was clean and exactly as advertised. I’d definitely recommend both Josh as a host and this location as a Cape getaway!

Family-Friendly 1BR Condo w/ Pools & Kitchenette
Great hosts! Would definitely stay again.

Stylish & Modern Studio Condo - Steps to the Beach
I had a fantastic experience during my stay! The place was exactly as described—clean, cozy, and well-equipped. The host was incredibly welcoming and responsive, making the check-in process a breeze. The location was perfect, with easy access to local attractions and restaurants. It truly felt like a home away from home. I would definitely recommend this place to anyone looking for a great stay. I can't wait to come back!

Sunny 2bedroom condo w pool, walk to town
We had a great time at Leah’s place. She is a terrific communicator, immediate responses. She also reached out to share about local fun events that were happening during our stay. So nice! We would definitely stay there again.

Ocean Edge Resort/Pool access/2bedroom-2bath Condo
We had a great stay with Rob in his cottage at Ocean Edge! The place had clearly been recently updated and it utilized space well such that it lived much bigger then its footprint. While it rained the whole time we were there, we could see Ocean Edge being a fun community for active folks. We highly recommend you stay here!
Quick stats about condo rentals in Dennis
Total rentals
80 properties
Nightly prices starting at
ﺩ.ﺇ220 before taxes and fees
Total number of reviews
3.1K reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Sagamore Beach
- Sandwich Glass Museum
- Owen Park Beach
- Coast Guard Beach
- New Silver Beach
- Onset Beach
- Nickerson State Park
- Oyster Harbors Beach
- Pinehills Golf Club
- Scusset Beach
- Inman Road Beach
- Kalmus Park Beach
- Ridgevale Beach
- Cahoon Hollow Beach
- Minot Beach
- Peggotty Beach
- Lighthouse Beach
- Forest Beach