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Chamberlain Vacation Packages

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Chamberlain Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Captain Sweetser's Inn

Captain Sweetser's Inn

2 out of 5
Price was $607, price is now $516 per person
$516
per person
Oct 4 - Oct 7
found 3 hours ago
Roundtrip flight included
Minneapolis (MSP) to Rockland (RKD)
Stay at this B&B in Searsport. Enjoy free breakfast, free WiFi, and 2 meeting rooms. Our guests praise the breakfast in our reviews. Popular attractions Penobscot Marine Museum and Long Cove are located nearby.
We can’t speak more highly of this impeccably run B&B. The house itself was spectacular….beautifully restored. Lori and Ginny, the owners, were so hospitable and lovely to chat with. Breakfast was excellent. Would highly recommend this place. Only a few minutes from the beautiful town of Belfast.

Reviewed on Jul 18, 2026

Trade Winds on the Bay

Trade Winds on the Bay

3.5 out of 5
Price was $687, price is now $598 per person
$598
per person
Oct 4 - Oct 7
found 3 hours ago
Roundtrip flight included
Minneapolis (MSP) to Rockland (RKD)
Stay at this aparthotel in Rockland. Enjoy free WiFi, free parking, and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Samoset Resort Golf Course and Project Puffin Visitor Center are located nearby.
the vue great - unable to access the swimming pool

Reviewed on Jul 21, 2026

Harborline Hotel

Harborline Hotel

3 out of 5
Price was $984, price is now $866 per person
$866
per person
Aug 26 - Aug 29
found 7 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rockland (RKD)
Stay at this hotel in Rockland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Samoset Resort Golf Course and Maine Lighthouse Museum are located nearby.
Basci clean however when u really lo9k in bathroom needs a serious cleaning. TV blurry, no breaksfast cold coffee, e things was pick over at 7am just not very appetizing room was dirty, the photography showed waterfront instead our view was in noisy parking lot . Will not stay again and I think I was charged incorrectly and will have to look into it.

Reviewed on Jul 22, 2026

The Craignair Inn & Restaurant

The Craignair Inn & Restaurant

3.5 out of 5
Price was $963, price is now $871 per person
$871
per person
Oct 4 - Oct 7
found 3 hours ago
Roundtrip flight included
Minneapolis (MSP) to Rockland (RKD)
Book a stay at this beach inn in Spruce Head. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tenants Harbor Marina and Birch Point Beach are located nearby.
Synday brunch was very good

Reviewed on Dec 22, 2025

Newly Renovated Charming House With Cozy Fireplace & Outdoor Entertainment Areas

Newly Renovated Charming House With Cozy Fireplace & Outdoor Entertainment Areas

2 out of 5
Price was $2,392, price is now $2,277 per person
$2,277
per person
Aug 26 - Aug 29
found 7 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rockland (RKD)
Book a stay at this golf vacation home in Rockport. Enjoy free parking. Popular attractions Samoset Resort Golf Course and Chickawaukie Pond are located nearby.

Spacious House With Modern Comforts and Nature

Spacious House With Modern Comforts and Nature

2 out of 5
Price was $2,107, price is now $2,009 per person
$2,009
per person
Aug 26 - Aug 29
found 7 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rockland (RKD)
Book a stay at this golf vacation home in Cushing. Enjoy free parking and laundry facilities. Popular attractions Maine State Prison Store and General Henry Knox Museum are located nearby.

Homeport Inn and Tavern

Homeport Inn and Tavern

3 out of 5
Price was $715, price is now $685 per person
$685
per person
Aug 29 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rockland (RKD)
Stay at this inn in Searsport. Enjoy daily housekeeping, a garden, and concierge services. Our guests praise the helpful staff in our reviews. Popular attractions Penobscot Marine Museum and Long Cove are located nearby.
This place was a delight! The room was great, we loved the pool room and breakfast was simple but perfect. Staff was really friendly and helpful too when I asked for a recommendation.

Reviewed on Jul 13, 2026

3 Bedroom 2 1/2 Bath Apartment With Views of Rocklan

3 Bedroom 2 1/2 Bath Apartment With Views of Rocklan

2 out of 5
Price was $1,632, price is now $1,563 per person
$1,563
per person
Aug 26 - Aug 29
found 7 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rockland (RKD)
Book a stay at this golf apartment in Rockland. Enjoy free parking, a marina, and a fitness center. Popular attractions Samoset Resort Golf Course and Sandy Beach are located nearby.

Chamberlain Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Captain Sweetser's Inn

Captain Sweetser's Inn

2 out of 5
Price was $607, price is now $516 per person
$516
per person
Oct 4 - Oct 7
found 3 hours ago
Roundtrip flight included
Minneapolis (MSP) to Rockland (RKD)
Trade Winds on the Bay

Trade Winds on the Bay

3.5 out of 5
Price was $687, price is now $598 per person
$598
per person
Oct 4 - Oct 7
found 3 hours ago
Roundtrip flight included
Minneapolis (MSP) to Rockland (RKD)
Harborline Hotel

Harborline Hotel

3 out of 5
Price was $984, price is now $866 per person
$866
per person
Aug 26 - Aug 29
found 7 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rockland (RKD)
Homeport Inn and Tavern

Homeport Inn and Tavern

3 out of 5
Price was $862, price is now $770 per person
$770
per person
Oct 4 - Oct 7
found 3 hours ago
Roundtrip flight included
Minneapolis (MSP) to Rockland (RKD)

Chamberlain Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Country Inn at Camden Rockport

The Country Inn at Camden Rockport

2.5 out of 5
Price was $1,283, price is now $1,157 per person
$1,157
per person
Sep 10 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Rockland (RKD)
Homeport Inn and Tavern

Homeport Inn and Tavern

3 out of 5
Price was $1,521, price is now $1,313 per person
$1,313
per person
Sep 23 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Rockland (RKD)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

JetBlue Airways
Tue, Aug 4 - Wed, Aug 12
BNA
Nashville Intl.
RKD
Knox County Regional
$469 Roundtrip, found 1 day ago
$469
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Aug 4 from Nashville Intl. to Knox County Regional, returning Wed, Aug 12, priced at $469 found 1 day ago
JetBlue Airways
Tue, Aug 4 - Tue, Aug 11
BNA
Nashville Intl.
RKD
Knox County Regional
$492 Roundtrip, found 1 day ago
$492
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Aug 4 from Nashville Intl. to Knox County Regional, returning Tue, Aug 11, priced at $492 found 1 day ago
JetBlue Airways
Tue, Aug 4 - Wed, Aug 12
BNA
Nashville Intl.
RKD
Knox County Regional
$513 Roundtrip, found 1 day ago
$513
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Aug 4 from Nashville Intl. to Knox County Regional, returning Wed, Aug 12, priced at $513 found 1 day ago
JetBlue Airways
Tue, Aug 4 - Fri, Aug 14
BNA
Nashville Intl.
RKD
Knox County Regional
$518 Roundtrip, found 1 day ago
$518
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Aug 4 from Nashville Intl. to Knox County Regional, returning Fri, Aug 14, priced at $518 found 1 day ago