Photo by Dawn Madden

Wenham Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Vacation Rentals in Wenham

Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

9.8 out of 10, Exceptional, (10)
"The house was clean, inviting, and cozy. The location was great. We very much enjoyed our stay there. "
The price is CA $429
CA $857 total
includes taxes & fees
Aug 6 - Aug 7
Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

Tuna Wharf Townhouse has been sold and is no longer available to rent.

10.0 out of 10, Exceptional, (78)
"Place was great, can’t beat the location, and Jonathan is honestly just the best. Top notch host and will definitely be staying at TWT again"
The price is CA $546
CA $898 total
includes taxes & fees
Aug 6 - Aug 7
Tuna Wharf Townhouse has been sold and is no longer available to rent.

Bell Buoy

3.5 star property
6.0 out of 10, (1)
"The property is nicely located but in need of updates. A lot of the lamps are plug in vs light switch and there were some flickering lights behind the TV. One lamp was missing a light bulb. No outlet in the bathroom for a hair dryer. The second bathroom is missing a door handle making it hard to open and close. We were unable to reach the ceiling fan chain without having to get on the bed, The Air Conditioner wasn't working on he first floor which made it a bit stuff but with open windows at...
The price is CA $209
CA $619 total
includes taxes & fees
Jul 23 - Jul 24
Bell Buoy

Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

2.0 star property
10.0 out of 10, Exceptional, (18)
"Easy walk to the beach and town. Great family space. "
The price is CA $387
CA $805 total
includes taxes & fees
Jul 20 - Jul 21
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

4 BR Home l Walk to Beaches & Downtown l Reserved Parking & Beach Gear included

8.0 out of 10, Very good, (1)
"Property was as listed, decorated in beachy coastal vibe. Kitchen was well equipped, space was ample and location was ideal for getting to downtown Rockport area. "
The price is CA $372
CA $843 total
includes taxes & fees
Jul 15 - Jul 16
4 BR Home l Walk to Beaches & Downtown l Reserved Parking & Beach Gear included

Classic New England: Big Family Home; Spas|Garden|FirePit; walk to beach, shops.

10.0 out of 10, Exceptional, (15)
"We had a great stay. Home was well appointed. Thank you!"
The price is CA $479
CA $1,476 total
includes taxes & fees
Jul 14 - Jul 15
Classic New England: Big Family Home; Spas|Garden|FirePit; walk to beach, shops.

Stay at Niles Beach

10.0 out of 10, Exceptional, (35)
" Allies ,Communication was excellent, house was clean cozy and peaceful, would definitely suggest if in Gloucester area!"
The price is CA $949
CA $1,734 total
includes taxes & fees
Jul 22 - Jul 23
Stay at Niles Beach

Oceanside Village Home~Private Fenced Yard~Reserved Parking

9.6 out of 10, Exceptional, (9)
"House was nice, with a great back yard. Just a short walk to beautiful rocks overlooking the ocean."
The price is CA $214
CA $585 total
includes taxes & fees
Jul 14 - Jul 15
Oceanside Village Home~Private Fenced Yard~Reserved Parking

3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

10.0 out of 10, Exceptional, (2)
"We stayed at this house for a week. Great location, quiet neighborhood, beds were confortable and communication with the host was great. We would definitely stay here again"
The price is CA $502
CA $1,001 total
includes taxes & fees
Jul 30 - Jul 31
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

❤️ of Cape Ann, - Historic Antique Colonial yet new & modern Close 2 Everything

9.6 out of 10, Exceptional, (26)
"Great stay"
The price is CA $737
CA $1,150 total
includes taxes & fees
Aug 6 - Aug 7
❤️ of Cape Ann, - Historic Antique Colonial yet new & modern Close 2 Everything

The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

2.0 star property
9.8 out of 10, Exceptional, (8)
"We had a lovely weekend! The views were beautiful and the location was great for our day trips. We will definitely be looking to rebook! "
The price is CA $539
CA $1,088 total
includes taxes & fees
Jul 16 - Jul 17
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

NEW 2BR Historic Marblehead Home+Minutes to Beach

2.0 star property
10.0 out of 10, Exceptional, (7)
"My family stayed in October for a quick weekend getaway. Great location and easy to get to from Boston. Would definitely book again. "
The price is CA $185
CA $548 total
includes taxes & fees
Jul 13 - Jul 14
NEW 2BR Historic Marblehead Home+Minutes to Beach

Rockmere Inn

3.5 star property
The price is CA $324
CA $1,154 total
includes taxes & fees
Jul 20 - Jul 21
Rockmere Inn

Downtown Marblehead 2brm/1.5bath w/ deck

10.0 out of 10, Exceptional, (1)
"The property was large with lots of natural light. Very clean and fully stocked for the stay."
The price is CA $377
CA $717 total
includes taxes & fees
Jul 24 - Jul 25
Downtown Marblehead 2brm/1.5bath w/ deck

Bright & Stylish 2BD/1BA in Town Center w Parking!

10.0 out of 10, Exceptional, (16)
"Definitely will be staying there again!"
The price is CA $419
CA $535 total
includes taxes & fees
Aug 5 - Aug 6
Bright & Stylish 2BD/1BA in Town Center w Parking!

Prime location in town w parking! Walk to beach, shops & harbor-Sleeps 8

10.0 out of 10, Exceptional, (14)
"Property as advertised. Great walkable location"
The price is CA $676
CA $1,211 total
includes taxes & fees
Jul 23 - Jul 24
Prime location in town w parking! Walk to beach, shops & harbor-Sleeps 8

Best location in Old Town home, 5 minutes to everything, enjoy the difference!

10.0 out of 10, Exceptional, (3)
"We are long time visitors of Marblehead and this has been one of, if not the best place we’ve stayed so far. The property was well appointed from the kitchen all the way to linens. A great central home that you will love!"
The price is CA $640
CA $1,239 total
includes taxes & fees
Jul 16 - Jul 17
Best location in Old Town home, 5 minutes to everything, enjoy the difference!

Authentic Rustic Single Family Home in Old Town

10.0 out of 10, Exceptional, (53)
"Natasha was excellent host. The house is perfect. Very cozy, clean and loved how it’s decorated. Close to everything. Adorable. "
The price is CA $391
CA $703 total
includes taxes & fees
Jul 16 - Jul 17
Authentic Rustic Single Family Home in Old Town

Spacious 5-bedroom 5 bath house in charming Marblehead & close to the ocean

9.8 out of 10, Exceptional, (6)
The price is CA $885
CA $1,217 total
includes taxes & fees
Jul 23 - Jul 24
Spacious 5-bedroom 5 bath house in charming Marblehead & close to the ocean

The widow’s walk your very own spa experience

10.0 out of 10, Exceptional, (14)
"Wife and I had a quick stay and loved Marblehead and the surrounding area. House was big but the lair was perfect little a lot for us. "
The price is CA $505
CA $942 total
includes taxes & fees
Jul 15 - Jul 16
The widow’s walk your very own spa experience
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Frequently asked questions

Can I find a vacation rental in Wenham?

Yes, we give you a choice of vacation rentals close to top local attractions in Wenham, or you can choose a more remote option if you'd like a relaxing place to stay. Wenham is known for its baseball games and riverfront. Make sure you have time to check out the restaurants and shopping during your trip.

What are some of the best vacation home rentals that Wenham has to offer?

"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester: Visitors like this Wenham vacation home rental. It offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

What can I see and do in Wenham?

Ipswich River and Pine and Hemlock Knoll are a couple of scenic spots to enjoy the outdoors, whereas Wenham Museum is one of the cultural attractions. In the larger area, you’ll find Encore Boston Harbor and North Shore Music Theatre.

What are vacation rentals like in Wenham?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Wenham. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a family trip or a small group gathering.