Annisquam River vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Annisquam River

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Home in Gloucester

4.96 out of 5 average rating, 121 reviews

Booking spring/summer-Overlooking Lobster Cove

Booking spring, summer and fall 2024 now. Water views/access, sunsets above Lobster Cove on Washington St. Ideal for couple, NEW KING BED in master, queen in 2nd. Fast WiFi./TV. Not suitable for young children. Central A/C. 2nd fl unit large windows. Open living/dining/kitchen area . 2 queen BR w new mattresses, sound machines, individual AC/heat. Overlooks beautiful Lobster Cove and footbridge. Minutes walk to the village of Annisquam and Lighthouse Beach. Small deck. Swim/kayak out your door.

Jan 20 – 27

R5,782 ZAR per night
Guest favorite

Condo in Rockport

4.99 out of 5 average rating, 143 reviews

Bearskin Neck Rockport ★ Amazing Views ★ Parking

From the deck of this New England vacation retreat enjoy amazing views of Rockport Harbor and the iconic Motif #1. Steps from delightful shops, restaurants, and ice cream & coffee shops, this recently updated 1-bedroom, 1-bathroom condo with rare, on-site parking is located in the heart of Rockport right on Bearskin Neck. Enjoy beautiful ocean breezes sipping coffee or cocktails on the deck of this sweet beach retreat nestled on the Atlantic coast. Come fall in love with charming Rockport!

Oct 4 – 11

R5,648 ZAR per night
Guest favorite

Guest suite in Gloucester

4.98 out of 5 average rating, 374 reviews

SplashLanding Private Beach Getaway in Gloucester

Jan-March 2024 open for monthly rentals. Must Book Summer 2024 via Airbnb website not the APP! *Our 2nd unit SquishInn has openings beginning April 2024 airbnb.com/h/squishinn-gloucester-ma Long walks on a private beach. Get sun-kissed; toes in the sand. Romantic dinners on the deck. Cozy in Winter (Energy Star home and Radiant heat throughout). TRAVELING WITH ANOTHER COUPLE? Book Private Beach Getaway SquishInn. Our 2nd unit for adult couples. Now another 2 friends can join you!

Oct 1 – 8

R7,004 ZAR per night

Popular amenities for Annisquam River vacation rentals

Other great vacation rentals in Annisquam River

Guest favorite

Guesthouse in Gloucester

4.94 out of 5 average rating, 143 reviews

Jestina's Cottage - Next to Rocky Neck

Sep 17 – 24

R3,083 ZAR per night
Guest favorite

Home in Gloucester

4.99 out of 5 average rating, 153 reviews

Rocky Neck Retreat 4 Bedroom/2Bath/Kitchen/Laundry

Aug 5 – 12

R9,989 ZAR per night
Guest favorite

Apartment in Rockport

4.94 out of 5 average rating, 148 reviews

Mary's By The Sea

Sep 9 – 16

R3,635 ZAR per night
Guest favorite

Home in Rockport

4.97 out of 5 average rating, 279 reviews

Charming Toe-Hold, A Short Walk to Town and Beach

Jan 3 – 10

R4,458 ZAR per night
Superhost

Home in Gloucester

4.93 out of 5 average rating, 123 reviews

Wonderful Rocky Neck home on Gloucester harbor

Nov 21 – 28

R7,375 ZAR per night
Guest favorite

Apartment in Ipswich

4.83 out of 5 average rating, 279 reviews

Cozy Apartment in New England .

Apr 25 – May 2

R2,546 ZAR per night
Guest favorite

Apartment in Rockport

4.93 out of 5 average rating, 122 reviews

Hidden Gem! Short term rental steps from 2 beaches

Dec 9 – 16

R3,609 ZAR per night
Guest favorite

Cottage in Gloucester

4.86 out of 5 average rating, 29 reviews

waterview guest suite

Dec 25 – Jan 1

R3,045 ZAR per night
Guest favorite

Guest suite in Gloucester

5.0 out of 5 average rating, 44 reviews

Sunsets at the Seawall - A Coastal Hideaway

Sep 9 – 16

R3,422 ZAR per night
Guest favorite

Condo in Rockport

4.89 out of 5 average rating, 37 reviews

In Town One Room Studio-Walk to Shops/Beaches

Apr 30 – May 7

R1,930 ZAR per night
Guest favorite

Loft in Gloucester

4.98 out of 5 average rating, 97 reviews

Downtown, Shops, Beach, Deck, Coffee Bar

Apr 25 – May 2

R3,008 ZAR per night
Guest favorite

Cottage in Gloucester

4.97 out of 5 average rating, 98 reviews

Sunny & private cottage in Lanesville Village

Nov 1 – 8

R4,900 ZAR per night

Other great vacation rentals in Annisquam River

Guest favorite

Vacation home in Gloucester

4.97 out of 5 average rating, 38 reviews

On the Water Gem - 2 BR -The Cove Lanesville

Nov 4 – 11

R9,350 ZAR per night
Guest favorite

Home in Gloucester

5.0 out of 5 average rating, 11 reviews

Waterfront with Breathtaking Views & Private Dock

Sep 7 – 14

R14,180 ZAR per night
Guest favorite

Guest suite in Gloucester

5.0 out of 5 average rating, 58 reviews

A charming Entire Guest Suite in Gloucester

Nov 21 – 28

R4,474 ZAR per night
Guest favorite

Vacation home in Gloucester

5.0 out of 5 average rating, 31 reviews

Gorgeous Oceanfront 2-Bdrm Apartment w/ Fireplace

Jul 6 – 13

R10,660 ZAR per night
Guest favorite

Condo in Ipswich

4.98 out of 5 average rating, 45 reviews

Private Ipswich Apartment

Dec 7 – 14

R2,989 ZAR per night
Guest favorite

Guesthouse in Gloucester

4.96 out of 5 average rating, 67 reviews

Plum Cove Cottage with king suite!

Sep 19 – 26

R4,530 ZAR per night
Superhost

Home in Gloucester

4.86 out of 5 average rating, 7 reviews

Rare 4BR Fully Renovated Oceanfront Home

Apr 7 – 14

R6,370 ZAR per night
Guest favorite

Apartment in Gloucester

5.0 out of 5 average rating, 20 reviews

Cozy Apartment at Green Landing in Gloucester

Oct 1 – 8

R3,397 ZAR per night
Superhost

Cottage in Rockport

5.0 out of 5 average rating, 16 reviews

Cottage with stunning ocean view and private beach

Oct 22 – 29

R14,206 ZAR per night
Guest favorite

Guesthouse in Rockport

5.0 out of 5 average rating, 56 reviews

Historic Carriage House | Downtown | Dog Friendly

Nov 19 – 26

R6,530 ZAR per night
Guest favorite

Guest suite in Gloucester

5.0 out of 5 average rating, 86 reviews

Walk to Good Harbor Beach and Downtown Gloucester

Jul 10 – 17

R3,658 ZAR per night
Guest favorite

Apartment in Gloucester

4.96 out of 5 average rating, 71 reviews

Beautifully remodeled unit in heart of Gloucester

Apr 4 – 11

R4,146 ZAR per night

Destinations to explore